Tolmetin supplier | CasNO.26171-23-3

Name
Tolmetin
EINECS 247-497-2
CAS No. 26171-23-3
Article Data25
CAS DataBase
Density 1.18 g/cm³
Solubility 222 mg/L in water
Melting Point 156 °C
Formula C₁₅H₁₅NO₃
Boiling Point 483.19 °C at 760 mmHg
Molecular Weight 257.289
Flash Point 246.025 °C
Transport Information
Appearance Off-white crystalline power
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Pyrrole-2-aceticacid, 1-methyl-5-p-toluoyl- (8CI);1-Methyl-5-p-toluoylpyrrole-2-acetic acid;5-[(p-Tolyl)carbonyl]-1-methylpyrrole-2-acetic acid;McN 2559;Tolmetine;
PSA 59.30000
LogP 2.19160

Synthetic route

: 52074-58-5
ethyl 2-(1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl)acetate

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water for 2h; Reflux;	100%
With sodium hydroxide for 0.5h; Heating;	95.2%
With water; sodium hydroxide at 60℃; for 2h; Temperature;	78.8%
With water at 70℃; for 24h; Alkaline conditions;	57.4 mg

: 26171-22-2
1-Methyl-5-(4-methylbenzoyl)pyrrole-2-acetonitrile

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Stage #1: 1-Methyl-5-(4-methylbenzoyl)pyrrole-2-acetonitrile With water; sodium hydroxide In ethanol for 6h; Reflux; Stage #2: With hydrogenchloride at 20℃;	98%
With sodium hydroxide In ethanol for 15h; Heating;	74%
With sodium hydroxide; sodium chloride In ethanol
In sodium hydroxide; ethanol
With sodium hydroxide; sodium chloride In ethanol

: 33369-52-7
methyl 1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water at 20℃;	98%
With water; sodium hydroxide at 60℃; for 2h; Temperature;	82.2%
Stage #1: methyl 1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate With water; sodium hydroxide at 20℃; for 48h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20℃; Inert atmosphere;	78%

: 35711-34-3
tolmetin sodium

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride In water	95%
With water at 20 - 25℃; for 1h; pH=1.5 - 4.0; Product distribution / selectivity; Acidic aqueous solution;
With water at 20℃; Acidic conditions;

: 1-Methyl-2-(2,2,2-trichloro-1-hydroxyethyl)-5-p-toluoylpyrrole

: 74-93-1
methylthiol

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide; ethyl acetate	89%

: C18H21NO3

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
With sodium hydroxide at 60℃; for 2h;	75%

: 1-methyl-2-formyl-5-p-methylbenzylpyrrole

: 75-25-2
Bromoform

: 75-08-1
ethanethiol

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile	70%

...Expand

: 1-Methyl-2-(2,2,2-trichloro-1-hydroxyethyl)-5-p-toluoylpyrrole

: 75-08-1
ethanethiol

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide; ethyl acetate	70%

: Tolmetin glucuronide

A: 6556-12-3, 489-91-8, 528-16-5, 552-12-5, 577-46-8, 643-33-4, 2240-07-5, 6294-16-2, 10133-02-5, 18402-78-3, 18968-14-4, 21179-08-8, 23018-83-9, 33599-45-0, 33599-46-1, 46171-67-9, 46171-69-1, 46172-26-3, 70021-34-0, 71031-08-8, 104195-06-4, 106499-29-0, 124817-72-7
D-glucuronic acid

B: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
With phosphate buffer at 37℃; for 6h; pH=7.4; Kinetics; Further Variations:; Reagents; Hydrolysis;

: 96-54-8
N-Methylpyrrole

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) POCl3 / 1) RT, 4 h, 2) 1,2-dichloroethane, 40 h 2: 50 percent / 1) POCl3 / 1) 1,2-dichloroethane, reflux, 30 min, 2) 50-60 deg C, 2 h 3: 60 percent / triton B / tetrahydrofuran / 4 h / Heating 4: 35 percent / HCl / ethanol / 70 h / Ambient temperature 5: 95.2 percent / 10percent aq. NaOH / 0.5 h / Heating View Scheme
Multi-step reaction with 5 steps 1.1: dichloromethane / 1 h / -10 - 0 °C / Inert atmosphere 1.2: 0.5 h / 0 °C / pH 10 / Inert atmosphere 1.3: 0.5 h / Inert atmosphere 2.1: hydrazine hydrate; potassium hydroxide / water / 8 h / 100 °C / Inert atmosphere 2.2: 20 °C / pH 2 / Inert atmosphere 3.1: toluene-4-sulfonic acid / 8 h / 70 °C / Inert atmosphere 4.1: DBN / toluene / 4 h / 115 °C / Inert atmosphere 5.1: water; sodium hydroxide / 48 h / 20 °C / Inert atmosphere 5.2: 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: dichloromethane / 1 h / -10 - 0 °C 1.2: 0.5 h / -10 - 0 °C / pH 10 2.1: hydrazine hydrate; potassium hydroxide / water / 5 h / 100 °C 3.1: potassium carbonate / dichloromethane / 3 h / 30 °C 4.1: o-xylene / 24 h / 145 °C 5.1: sodium hydroxide / methanol; water / 2 h / 30 °C View Scheme

: 75820-72-3
1-metil-5-p-metilbenzoil-1H-pirrolo-2-carbossialdeide

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / triton B / tetrahydrofuran / 4 h / Heating 2: 35 percent / HCl / ethanol / 70 h / Ambient temperature 3: 95.2 percent / 10percent aq. NaOH / 0.5 h / Heating View Scheme

: 85380-92-3
1-(methylsulfinyl)-1-methylthio-2-(1-methyl-5-p-toluoyl-2-pyrrolyl)ethylene

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / HCl / ethanol / 70 h / Ambient temperature 2: 95.2 percent / 10percent aq. NaOH / 0.5 h / Heating View Scheme

: 62128-31-8
(1-methyl-1H-pyrrol-2-yl)-p-tolylmethanone

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 50 percent / 1) POCl3 / 1) 1,2-dichloroethane, reflux, 30 min, 2) 50-60 deg C, 2 h 2: 60 percent / triton B / tetrahydrofuran / 4 h / Heating 3: 35 percent / HCl / ethanol / 70 h / Ambient temperature 4: 95.2 percent / 10percent aq. NaOH / 0.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: triphenylphosphine; sodium periodate; sodium acetate; acetic acid; manganese (II) acetate tetrahydrate / 24 h / 70 °C / Inert atmosphere 2: water / 24 h / 70 °C / Alkaline conditions View Scheme

: 63833-44-3
morpholino(p-tolyl)methanone

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) POCl3 / 1) RT, 4 h, 2) 1,2-dichloroethane, 40 h 2: 50 percent / 1) POCl3 / 1) 1,2-dichloroethane, reflux, 30 min, 2) 50-60 deg C, 2 h 3: 60 percent / triton B / tetrahydrofuran / 4 h / Heating 4: 35 percent / HCl / ethanol / 70 h / Ambient temperature 5: 95.2 percent / 10percent aq. NaOH / 0.5 h / Heating View Scheme

: 21898-59-9
1-methylpyrrole-2-acetic acid

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / 8 h / 70 °C / Inert atmosphere 2.1: DBN / toluene / 4 h / 115 °C / Inert atmosphere 3.1: water; sodium hydroxide / 48 h / 20 °C / Inert atmosphere 3.2: 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / dichloromethane / 3 h / 30 °C 2: o-xylene / 24 h / 145 °C 3: sodium hydroxide / methanol; water / 2 h / 30 °C View Scheme

: 21898-43-1
2-(1-methyl-1H-pyrrol-2-yl)-2-oxoacetic acid

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrazine hydrate; potassium hydroxide / water / 8 h / 100 °C / Inert atmosphere 1.2: 20 °C / pH 2 / Inert atmosphere 2.1: toluene-4-sulfonic acid / 8 h / 70 °C / Inert atmosphere 3.1: DBN / toluene / 4 h / 115 °C / Inert atmosphere 4.1: water; sodium hydroxide / 48 h / 20 °C / Inert atmosphere 4.2: 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: hydrazine hydrate; potassium hydroxide / water / 5 h / 100 °C 2: potassium carbonate / dichloromethane / 3 h / 30 °C 3: o-xylene / 24 h / 145 °C 4: sodium hydroxide / methanol; water / 2 h / 30 °C View Scheme

: 51856-79-2
N-methyl-2-(methoxycarbonylmethyl)pyrrole

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: DBN / toluene / 4 h / 115 °C / Inert atmosphere 2.1: water; sodium hydroxide / 48 h / 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: o-xylene / 24 h / 145 °C 2: sodium hydroxide / methanol; water / 2 h / 30 °C View Scheme
Multi-step reaction with 4 steps 1.1: 1-amino-3-(dimethylamino)propane / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux 1.2: 0.5 h / 20 °C 2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / 18 h / 70 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h 4.1: sodium hydroxide / methanol; tetrahydrofuran; water / 16 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 1-amino-3-(dimethylamino)propane / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux 1.2: 0.5 h / 20 °C 2.1: bis(dibenzylideneacetone)-palladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N,N,N,N,-tetramethylethylenediamine / N,N-dimethyl-formamide / 0.06 h / 160 °C / Sealed tube; Microwave irradiation 3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h 4.1: sodium hydroxide / methanol; tetrahydrofuran; water / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 4-methyl-morpholine / o-xylene / 12 h / Reflux 2: sodium hydroxide; water / 2 h / 60 °C View Scheme

: 1711-02-0
4-iodobenzoic acid chloride

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 1-amino-3-(dimethylamino)propane / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux 1.2: 0.5 h / 20 °C 2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / 18 h / 70 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h 4.1: sodium hydroxide / methanol; tetrahydrofuran; water / 16 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: 1-amino-3-(dimethylamino)propane / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux 1.2: 0.5 h / 20 °C 2.1: bis(dibenzylideneacetone)-palladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N,N,N,N,-tetramethylethylenediamine / N,N-dimethyl-formamide / 0.06 h / 160 °C / Sealed tube; Microwave irradiation 3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h 4.1: sodium hydroxide / methanol; tetrahydrofuran; water / 16 h / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: 1-amino-3-(dimethylamino)propane / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux
1.2: 0.5 h / 20 °C
2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / 18 h / 70 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h
4.1: sodium hydroxide / methanol; tetrahydrofuran; water / 16 h / 20 °C
View Scheme

Multi-step reaction with 4 steps
1.1: 1-amino-3-(dimethylamino)propane / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / Reflux
1.2: 0.5 h / 20 °C
2.1: bis(dibenzylideneacetone)-palladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N,N,N,N,-tetramethylethylenediamine / N,N-dimethyl-formamide / 0.06 h / 160 °C / Sealed tube; Microwave irradiation
3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h
4.1: sodium hydroxide / methanol; tetrahydrofuran; water / 16 h / 20 °C
View Scheme

: methyl 2-(5-(4-iodobenzoyl)-1-methyl-1H-pyrrol-2-yl)acetate

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: bis(dibenzylideneacetone)-palladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N,N,N,N,-tetramethylethylenediamine / N,N-dimethyl-formamide / 0.06 h / 160 °C / Sealed tube; Microwave irradiation 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h 3: sodium hydroxide / methanol; tetrahydrofuran; water / 16 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / 18 h / 70 °C 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h 3: sodium hydroxide / methanol; tetrahydrofuran; water / 16 h / 20 °C View Scheme

: 617721-38-7
methyl 2-(5-(4-cyanobenzoyl)-1-methyl-1H-pyrrol-2-yl)acetate

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 3 h 2: sodium hydroxide / methanol; tetrahydrofuran; water / 16 h / 20 °C View Scheme

: 24437-41-0
1-methyl-2-pyrroleacetonitrile

: 874-60-2
4-methyl-benzoyl chloride

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminium trichloride / 1,1-dichloroethane; hexane; benzene 2: sodium hydroxide; sodium chloride / ethanol View Scheme

: [1-(pyrimidin-2-yl)-1H-pyrrol-2-yl](p-tolyl)methanone

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium ethanolate / dimethyl sulfoxide / 3 h / 100 °C / Inert atmosphere 2: sodium hydride / N,N-dimethyl-formamide / 3.5 h / 20 °C 3: triphenylphosphine; sodium periodate; sodium acetate; acetic acid; manganese (II) acetate tetrahydrate / 24 h / 70 °C / Inert atmosphere 4: water / 24 h / 70 °C / Alkaline conditions View Scheme

: 55895-62-0
2-(4-methylbenzoyl)pyrrole

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 3.5 h / 20 °C 2: triphenylphosphine; sodium periodate; sodium acetate; acetic acid; manganese (II) acetate tetrahydrate / 24 h / 70 °C / Inert atmosphere 3: water / 24 h / 70 °C / Alkaline conditions View Scheme

: 104-87-0
4-methyl-benzaldehyde

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: tert.-butylhydroperoxide; palladium diacetate; Trimethylacetic acid / toluene; decane / 1.5 h / 60 °C / Inert atmosphere; Sealed tube 2: sodium ethanolate / dimethyl sulfoxide / 3 h / 100 °C / Inert atmosphere 3: sodium hydride / N,N-dimethyl-formamide / 3.5 h / 20 °C 4: triphenylphosphine; sodium periodate; sodium acetate; acetic acid; manganese (II) acetate tetrahydrate / 24 h / 70 °C / Inert atmosphere 5: water / 24 h / 70 °C / Alkaline conditions View Scheme

Yield

Multi-step reaction with 5 steps
1: tert.-butylhydroperoxide; palladium diacetate; Trimethylacetic acid / toluene; decane / 1.5 h / 60 °C / Inert atmosphere; Sealed tube
2: sodium ethanolate / dimethyl sulfoxide / 3 h / 100 °C / Inert atmosphere
3: sodium hydride / N,N-dimethyl-formamide / 3.5 h / 20 °C
4: triphenylphosphine; sodium periodate; sodium acetate; acetic acid; manganese (II) acetate tetrahydrate / 24 h / 70 °C / Inert atmosphere
5: water / 24 h / 70 °C / Alkaline conditions
View Scheme

: C10H13NO4

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2 h / 190 °C 2: 4-methyl-morpholine / o-xylene / 12 h / Reflux 3: sodium hydroxide; water / 2 h / 60 °C View Scheme

: C11H15NO4

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2 h / 190 °C 2: 4-methyl-morpholine / o-xylene / 12 h / Reflux 3: sodium hydroxide / 2 h / 60 °C View Scheme

: C10H15NO2

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4-methyl-morpholine / o-xylene / 12 h / Reflux 2: sodium hydroxide / 2 h / 60 °C View Scheme

: 83863-74-5
2-(carboxymethyl)-1-methyl-1H-pyrrole-3-carboxylic acid

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / 1 h / Reflux 2: 2 h / 190 °C 3: 4-methyl-morpholine / o-xylene / 12 h / Reflux 4: sodium hydroxide; water / 2 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 1 h / Reflux 2: 2 h / 190 °C 3: 4-methyl-morpholine / o-xylene / 12 h / Reflux 4: sodium hydroxide / 2 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid / 1 h / Reflux 2: 2 h / 190 °C 3: 4-methyl-morpholine / o-xylene / 12 h / Reflux 4: sodium hydroxide; water / 2 h / 60 °C View Scheme

: C9H11NO4

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2 h / 190 °C 2: 4-methyl-morpholine / o-xylene / 12 h / Reflux 3: sodium hydroxide; water / 2 h / 60 °C View Scheme

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: 85622-93-1
temozolomide

: 33369-52-7
methyl 1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 60℃; for 6h; Sealed tube;	81%

: 67-56-1
methanol

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: 33369-52-7
methyl 1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate

Conditions

Conditions	Yield
With sulfuric acid for 3h; Reflux;	77%
With sulfuric acid for 3h; Reflux;

: 1111-72-4
carbon dioxide

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: [13C]tolmetin

Conditions

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 0.0833333h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;	75%
Stage #1: 1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid With caesium carbonate In methanol at 20℃; for 1h; Inert atmosphere; Stage #2: carbon dioxide In dimethyl sulfoxide at 150℃; for 0.0833333h; Inert atmosphere; Cooling with liquid nitrogen;	5.7 mg

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: 90-05-1
2-methoxy-phenol

: 1207070-76-5
1-methyl-5-p-toluoylpyrrole-2-acetamidoacetic acid isopropyl alcohol ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 30℃;	70%

: 2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: 3-trifluoromethylthiotolemtin

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; bis(4-methoxyphenyl)selenide In chloroform at 20℃; for 16h; Reagent/catalyst;	70%

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: C14H14(2)HNO

Conditions

Conditions	Yield
With 2,4,6-trimethyl-pyridine; 2,4,6-Triisopropylthiophenol; water-d2; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane Irradiation;	69%

: 6265-73-2
N-(2-hydroxyethyl)nicotinamide

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: 761415-92-3
[1-methyl-5-(4-methyl-benzoyl)-1H-pyrrol-2-yl]-acetic acid 2-[(pyridine-3-carbonyl)-amino]-ethyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetonitrile	68%

: 753-90-2
trifluoroethylamine

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: 75-05-8
acetonitrile

: N-acetyl-2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]-N-(2,2,2-trifluoroethyl)acetamide

Conditions

Conditions	Yield
With copper(l) iodide; tert.-butylnitrite at 65℃; for 12h;	67%

...Expand

: 75368-99-9
amino acetic acid guacil ester hydrochloride

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: amtolmetin guacil

Conditions

Conditions	Yield
With potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide In acetone at -5 - 30℃; for 5h;	60%

: 887144-97-0
Togni's reagent

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: (1-methyl-5-(2,2,2-trifluoroethyl)-1H-pyrrol-2-yl)(p-tolyl)methanone

Conditions

Conditions	Yield
With 2,2'-dipyridyl ketone; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; copper dichloride; N,N,N',N'-tetramethylguanidine In ethyl acetate at 20℃; for 12h; Inert atmosphere; Irradiation; Sealed tube; chemoselective reaction;	43%

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: 62128-36-3
1,5-dimethyl-2-(4-methylbenzoyl)pyrrole

Conditions

Conditions	Yield
In water Rate constant; Mechanism; Irradiation;

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

A: 62128-36-3
1,5-dimethyl-2-(4-methylbenzoyl)pyrrole

B: (1-methyl-5-{2-[1-methyl-5-(4-methyl-benzoyl)-1H-pyrrol-2-yl]-ethyl}-1H-pyrrol-2-yl)-p-tolyl-methanone

Conditions

Conditions	Yield
With copper(II) ion In water pH=7.4; Product distribution; Kinetics; Further Variations:; Reagents; various Cu(2+) concentrations; also in the absence of Cu(2+); Decarboxylation; photodecarboxylation; Irradiation;

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: C15H11(3)H4NO3

Conditions

Conditions	Yield
With tritium; Crabtree's catalyst In dichloromethane
With tritium; Crabtree's catalyst regioselective reaction;

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: (3)H3C15H12NO3

Conditions

Conditions	Yield
With tritium; polystyrene-bound PPh3-[(COD)Ir(PCy3)(Py)]PF6 complex In dichloromethane at 20℃; for 3h;

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: [1-methyl-5-(4-methyl-benzoyl)-1H-pyrrol-2-yl]-acetic acid 2-[(1-methyl-1,4-dihydro-pyridine-3-carbonyl)-amino]-ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 68 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / acetonitrile 2: 79 percent / CH2Cl2; acetonitrile / 144 h / 20 °C 3: 100 percent / NaHCO3; Na2S2O4 / H2O; ethyl acetate / 0.25 h / 0 °C / pH 7 View Scheme

: 26171-23-3
1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

: 1-methyl-3-(2-{[1-methyl-5-(4-methyl-benzoyl)-1H-pyrrol-2-yl]-acetoxy}-ethylcarbamoyl)-pyridinium; iodide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 68 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / acetonitrile 2: 79 percent / CH2Cl2; acetonitrile / 144 h / 20 °C View Scheme

Tolmetin Specification

The Tolmetin, with the CAS registry number 26171-23-3, is also known as 2-[1-Methyl-5-(4-methylbenzoyl)-pyrrol-2-yl]acetic acid. It belongs to the product category of API intermediates. Its EINECS number is 247-497-2. This chemical's molecular formula is C₁₅H₁₅NO₃ and molecular weight is 257.29. What's more, its systematic name is [1-Methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid. Its classification codes are: (1)Analgesics; (2)Analgesics, Non-Narcotic; (3)Anti-Inflammatory Agents; (4)Anti-inflammatory; (5)Anti-inflammatory agents, non-steroidal; (6)Antirheumatic Agents; (7)Cyclooxygenase inhibitors; (8)Drug / Therapeutic Agent; (9)Enzyme Inhibitors; (10)Peripheral Nervous System Agents; (11)Reproductive Effect; (12)Sensory System Agents. This chemical is a non-steroidal anti-inflammatory drug of the arylalkanoic acids. It is used primarily to reduce hormones that cause pain, swelling, tenderness, and stiffness in conditions such as osteoarthritis and rheumatoid arthritis, including juvenile rheumatoid arthritis.

Physical properties of Tolmetin are: (1)ACD/LogP: 2.68; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.38; (4)ACD/LogD (pH 7.4): -0.39; (5)ACD/BCF (pH 5.5): 3.23; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 34.50; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 59.3 Å²; (13)Index of Refraction: 1.582; (14)Molar Refractivity: 72.717 cm³; (15)Molar Volume: 217.982 cm³; (16)Polarizability: 28.827×10^-24cm³; (17)Surface Tension: 43.56 dyne/cm; (18)Density: 1.18 g/cm³; (19)Flash Point: 246.025 °C; (20)Enthalpy of Vaporization: 78.814 kJ/mol; (21)Boiling Point: 483.19 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by [1-methyl-5-(4-methyl-benzoyl)-1H-pyrrol-2-yl]-acetic acid ethyl ester by heating. This reaction will need reagent 10percent aq. NaOH with the reaction time of 30 min. The yield is about 95.2%.

Tolmetin can be prepared by [1-methyl-5-(4-methyl-benzoyl)-1H-pyrrol-2-yl]-acetic acid ethyl ester by heating

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1ccc(n1C)CC(=O)O)c2ccc(cc2)C
(2)Std. InChI: InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
(3)Std. InChIKey: UPSPUYADGBWSHF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mammal (species unspecified)	LD50	oral	300mg/kg (300mg/kg)		Indian Journal of Medical Research. Vol. 81, Pg. 621, 1985.
mouse	LD50	intraperitoneal	600mg/kg (600mg/kg)		Farmaco, Edizione Scientifica. Vol. 38, Pg. 90, 1983.
mouse	LD50	intravenous	680mg/kg (680mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 45, 1977.
mouse	LD50	oral	914mg/kg (914mg/kg)		Farmaco, Edizione Scientifica. Vol. 38, Pg. 90, 1983.
mouse	LD50	unreported	1107mg/kg (1107mg/kg)		Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 19, Pg. 460, 1984.
rat	LD50	oral	293mg/kg (293mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH	Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1526, 1975.
rat	LD50	rectal	744mg/kg (744mg/kg)		Archivos de Farmacologia y Toxicologia. Vol. 5, Pg. 257, 1979.

Product Name

Tolmetin

Synthetic route

Tolmetin Specification

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