2-Amino-5-chloro-N,3-dimethylbenzamide supplier

Name
Bardoxolone
EINECS 618-233-7
CAS No. 890707-28-5
Article Data26
CAS DataBase
Density 1.239g/cm³
Solubility
Melting Point 130-132 °C
Formula C₉H₁₁ClN₂O
Boiling Point 308.8 °C at 760 mmHg
Molecular Weight 198.652
Flash Point 140.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Amino-5-chloro-N,3-dimethylhenzamide
PSA 58.61000
LogP 2.74620

Synthetic route

: 79101-83-0
2-amino-3-methyl-5-chlorobenzoic acid methyl ester

: 74-89-5
methylamine

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
In methanol at 65 - 68℃; for 5h; Temperature;	98%
In methanol at 45℃; for 6h;	97.2%
In ethylene glycol; acetonitrile at 0 - 70℃; for 17.5 - 23h; Product distribution / selectivity;	84.8%

: isopropyl 2-amino-5-chloro-3-methylbenzoate

: 74-89-5
methylamine

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
In isopropyl alcohol at 60℃; for 7h;	96.8%

: 2-amino-5-chloro-3-methylbenzoic acid ethyl ester

: 74-89-5
methylamine

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
In methanol at 50℃; for 6h;	95.4%

: 120374-68-7
6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

: 74-89-5
methylamine

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
With acetic acid In ethyl acetate at 35 - 45℃; for 0.333333h;	95%
With acetic acid In ethyl acetate at 22 - 52℃; for 0.333333 - 2.75h; Product distribution / selectivity;	93%
With acetic acid In water; acetonitrile at 25 - 30℃; for 2.5h; Product distribution / selectivity;	87%

: 120374-68-7
6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

: 593-51-1
methylamine hydrochloride

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
With potassium hydrogencarbonate In acetonitrile at 25 - 30℃; for 3h; Solvent; Reagent/catalyst; Temperature;	93.6%
Stage #1: methylamine hydrochloride With triethylamine In dichloromethane at 20℃; for 2h; Stage #2: 6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione With acetic acid In dichloromethane; ethyl acetate Reflux;
With potassium carbonate In ethanol at 25 - 80℃; for 5.5h; Reagent/catalyst; Temperature;

: 20776-67-4
2-amino-5-chloro-3-methylbenzoic acid

: 74-89-5
methylamine

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Stage #1: 2-amino-5-chloro-3-methylbenzoic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20℃; for 2h; Stage #2: methylamine In dichloromethane at 0℃; for 2h; Temperature;	92.6%
Stage #1: 2-amino-5-chloro-3-methylbenzoic acid With thionyl chloride for 3h; Reflux; Stage #2: methylamine In tetrahydrofuran; water at 20℃; Cooling with ice;	59.3%
Stage #1: 2-amino-5-chloro-3-methylbenzoic acid With thionyl chloride for 3h; Reflux; Stage #2: methylamine In tetrahydrofuran; water at 20℃; for 12h; Cooling with ice;	59.3%

: 120374-68-7
6-chloro-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

: 74-89-5
methylamine

A: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

B: 6-chloro-3,8-dimethyl-2,4(1H,3H)-quinazolinedione

C: 20776-67-4
2-amino-5-chloro-3-methylbenzoic acid

Conditions

Conditions	Yield
With water; acetic acid In ethyl acetate at 48 - 52℃; for 1h; Product distribution / selectivity;	A 87.3% B 3.4% C 1.7%

...Expand

: 870997-57-2
N-methyl-3-methyl-2-aminobenzamide

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; acetic acid at 5 - 20℃;	85%
Stage #1: N-methyl-3-methyl-2-aminobenzamide With hydrogenchloride In N,N-dimethyl-formamide at 10 - 30℃; Stage #2: With sodium sulfite In water; N,N-dimethyl-formamide at 30 - 35℃; for 3.25h; Stage #3: With sodium hydroxide; sodium sulfite In water; N,N-dimethyl-formamide at 10℃; for 0.25h; pH=2.2; Product distribution / selectivity;	72.7%
With N-chloro-succinimide In acetonitrile for 1h; Reflux;
With sulfuryl dichloride In dichloromethane at 0 - 30℃;
With thionyl chloride In acetonitrile at 40 - 50℃;

: 201230-82-2
carbon monoxide

: 146948-68-7
2-bromo-4-chloro-6-methylphenylamine

: 74-89-5
methylamine

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
palladium diacetate; 1,4-di(diphenylphosphino)-butane In ethylene glycol at 25 - 110℃; under 2842.59 Torr; Inert atmosphere; Sealed tube;	70%

...Expand

: 2-amino-5-chloro-3-methylbenzoyl chloride

: 74-89-5
methylamine

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
In dichloromethane
In dichloromethane

: 20776-67-4
2-amino-5-chloro-3-methylbenzoic acid

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / Reflux 2: dichloromethane View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 3 h / Reflux 2: dichloromethane View Scheme
Multi-step reaction with 2 steps 1.1: 1,4-dioxane / 2 h / 50 °C 2.1: triethylamine / dichloromethane / 2 h / 20 °C 2.2: Reflux View Scheme

: 1391132-23-2
2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate

: 1391132-24-3
2-(dimethylamino)ethyl 2-amino-5-chloro-3-methylbenzoate

: 74-89-5
methylamine

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
at 110℃; under 3876.26 Torr; for 6.06667h; Product distribution / selectivity; Sealed tube; Inert atmosphere;

...Expand

: 4389-45-1
3-methylantranilic acid

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 2.1: thionyl chloride / 3 h / Reflux 2.2: 20 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 2.1: thionyl chloride / 3 h / Reflux 2.2: 12 h / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / Cooling with ice 2: N-chloro-succinimide / acetonitrile / 1 h / Reflux View Scheme

: 95-53-4
o-toluidine

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium sulfate / water / 40 °C 1.2: Reflux 2.1: sulfuric acid / 0.33 h / 80 °C 3.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C 4.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 5.1: thionyl chloride / 3 h / Reflux 5.2: 20 °C / Cooling with ice View Scheme
Multi-step reaction with 5 steps 1.1: sodium sulfate / water / 40 °C 1.2: 0.17 h / Reflux 2.1: sulfuric acid / 60 - 80 °C 3.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C 3.2: pH 4 4.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 5.1: thionyl chloride / 3 h / Reflux 5.2: 12 h / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 5 steps 1.1: sodium sulfate; hydrogenchloride; hydroxylamine hydrochloride / water / 0.17 h / Reflux 2.1: sulfuric acid / 0.83 h / 70 - 80 °C 3.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C 4.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 5.1: thionyl chloride / 3 h / Reflux 5.2: 12 h / 20 °C / Cooling with ice View Scheme

: 1132-03-2
2-(hydroxyimino)-N-(2-methylphenyl)acetamide

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sulfuric acid / 0.33 h / 80 °C 2.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 4.1: thionyl chloride / 3 h / Reflux 4.2: 20 °C / Cooling with ice View Scheme
Multi-step reaction with 4 steps 1.1: sulfuric acid / 60 - 80 °C 2.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C 2.2: pH 4 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 4.1: thionyl chloride / 3 h / Reflux 4.2: 12 h / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 4 steps 1.1: sulfuric acid / 0.83 h / 70 - 80 °C 2.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C 3.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 4.1: thionyl chloride / 3 h / Reflux 4.2: 12 h / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / 1,2-dichloro-ethane / 12 h / 0 - 30 °C 2.1: acetic acid; dihydrogen peroxide / 0.25 h / 5 °C 2.2: 28.17 h / 5 - 20 °C 2.3: 3.75 h / 10 - 40 °C 3.1: acetic acid / ethyl acetate / 3.25 h / 0 - 25 °C / pH 9 - 10 View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / 1,2-dichloro-ethane / 12 h / 0 - 30 °C 2.1: acetic acid; dihydrogen peroxide / 0.25 h / 5 °C 2.2: 28.17 h / 5 - 20 °C 2.3: 3.75 h / 10 - 40 °C 3.1: potassium carbonate / ethanol / 5.5 h / 25 - 80 °C View Scheme

: 1127-59-9
7-methyl-1H-indole-2,3-dione

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 3.1: thionyl chloride / 3 h / Reflux 3.2: 20 °C / Cooling with ice View Scheme
Multi-step reaction with 3 steps 1.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C 1.2: pH 4 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 3.1: thionyl chloride / 3 h / Reflux 3.2: 12 h / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 3 steps 1.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C 2.1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.67 h / 100 °C 3.1: thionyl chloride / 3 h / Reflux 3.2: 12 h / 20 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1.1: acetic acid; dihydrogen peroxide / 0.25 h / 5 °C 1.2: 28.17 h / 5 - 20 °C 1.3: 3.75 h / 10 - 40 °C 2.1: acetic acid / ethyl acetate / 3.25 h / 0 - 25 °C / pH 9 - 10 View Scheme
Multi-step reaction with 3 steps 1: sulfuryl dichloride; acetic acid / 120 - 125 °C 2: sulfuric acid; acetic acid; dihydrogen peroxide / 60 - 65 °C 3: ethyl acetate / 20 °C View Scheme

: 65-85-0
benzoic acid

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: acetic acid; chlorine / 3 h / 30 - 40 °C / Inert atmosphere 2.1: 0.08 h 2.2: Grignard reagent / 1 h 3.1: sulfuric acid; nitric acid / 1 h / 0 - 40 °C 4.1: zinc; sodium hydroxide / 2 h / 70 °C 5.1: diisopropyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C 5.2: 2 h / 0 °C View Scheme

: 51-36-5
3,5-dichlorobenzoic acid

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 0.08 h 1.2: Grignard reagent / 1 h 2.1: sulfuric acid; nitric acid / 1 h / 0 - 40 °C 3.1: zinc; sodium hydroxide / 2 h / 70 °C 4.1: diisopropyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C 4.2: 2 h / 0 °C View Scheme

: 56961-33-2
3-Chloro-5-Methylbenzoic Acid

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid; nitric acid / 1 h / 0 - 40 °C 2.1: zinc; sodium hydroxide / 2 h / 70 °C 3.1: diisopropyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C 3.2: 2 h / 0 °C View Scheme

: 108-88-3
toluene

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: oxygen; cobalt(II) aceylacetonate; N-hydroxyphthalimide / dichloromethane / 1 h / 30 °C / 22502.3 Torr / Sealed tube 2.1: acetic acid; chlorine / 3 h / 30 - 40 °C / Inert atmosphere 3.1: 0.08 h 3.2: Grignard reagent / 1 h 4.1: sulfuric acid; nitric acid / 1 h / 0 - 40 °C 5.1: zinc; sodium hydroxide / 2 h / 70 °C 6.1: diisopropyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C 6.2: 2 h / 0 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: oxygen; cobalt(II) aceylacetonate; N-hydroxyphthalimide / dichloromethane / 1 h / 30 °C / 22502.3 Torr / Sealed tube
2.1: acetic acid; chlorine / 3 h / 30 - 40 °C / Inert atmosphere
3.1: 0.08 h
3.2: Grignard reagent / 1 h
4.1: sulfuric acid; nitric acid / 1 h / 0 - 40 °C
5.1: zinc; sodium hydroxide / 2 h / 70 °C
6.1: diisopropyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C
6.2: 2 h / 0 °C
View Scheme

: 30273-00-8
2-methyl-4,6-dichloroaniline

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: copper bromide / N,N-dimethyl-formamide / 18 h / 90 - 95 °C 2: sodium hydroxide / 10 h / 70 - 75 °C 3: sulfuric acid / 16 h / Reflux 4: methanol / 5 h / 65 - 68 °C View Scheme

: 939990-03-1
2-amino-5-chloro-3-methylbenzonitrile

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / 10 h / 70 - 75 °C 2: sulfuric acid / 16 h / Reflux 3: methanol / 5 h / 65 - 68 °C View Scheme

: 5437-38-7
3-methyl-2-nitrobenzoic acid

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen / ethanol / 4 h / 50 °C / 1500.15 Torr 2: chlorine / 1,2-dichloro-ethane / 3 h / 50 °C 3: sulfuric acid / 6 h / 5 °C / Reflux 4: isopropyl alcohol / 7 h / 60 °C View Scheme
Multi-step reaction with 4 steps 1: hydrogen / ethanol / 4 h / 50 °C / 1500.15 Torr 2: chlorine / 1,2-dichloro-ethane / 3 h / 50 °C 3: sulfuric acid / 6 h / 5 °C / Reflux 4: methanol / 6 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1: hydrogen / ethanol / 4 h / 50 °C / 1500.15 Torr 2: chlorine / 1,2-dichloro-ethane / 3 h / 50 °C 3: sulfuric acid / 8 h / 5 °C / Reflux 4: methanol / 6 h / 45 °C View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / toluene / 90 - 100 °C 1.2: 0 - 10 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol 3.1: acetic acid; hydrogenchloride; dihydrogen peroxide / 5 - 20 °C View Scheme
Multi-step reaction with 4 steps 1: pyrographite; hydrazine hydrate; sodium hydroxide; iron(III) chloride hexahydrate / water / 70 °C 2: pyridine / acetonitrile / 4 h / 50 - 60 °C 3: acetic acid / water; acetonitrile / 1 h / Reflux 4: thionyl chloride / acetonitrile / 40 - 50 °C View Scheme

: 99-04-7
m-Toluic acid

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: nitric acid / -10 - -5 °C 2.1: thionyl chloride / toluene / 90 - 100 °C 2.2: 0 - 10 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol 4.1: acetic acid; hydrogenchloride; dihydrogen peroxide / 5 - 20 °C View Scheme

: 600126-70-3
N,3-dimethyl-2-nitrobenzamide

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol 2: acetic acid; hydrogenchloride; dihydrogen peroxide / 5 - 20 °C View Scheme

: 66176-17-8
6-methylisatoic anhydride

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / water; acetonitrile / 1 h / Reflux 2: thionyl chloride / acetonitrile / 40 - 50 °C View Scheme

: 14389-06-1
5-chloro-7-methyl-1H-indole-2,3-dione

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; acetic acid; dihydrogen peroxide / 60 - 65 °C 2: ethyl acetate / 20 °C View Scheme

: (E)-2-(hydroxyimino)-N-(o-tolyl)acetamide

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 60 - 65 °C 2: sulfuryl dichloride; acetic acid; dihydrogen peroxide / 60 - 125 °C 3: ethyl acetate / 20 °C View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid / 60 - 65 °C 2: sulfuryl dichloride; acetic acid / 120 - 125 °C 3: sulfuric acid; acetic acid; dihydrogen peroxide / 60 - 65 °C 4: ethyl acetate / 20 °C View Scheme

: 500011-86-9
3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 500008-45-7
rynaxypyr

Conditions

Conditions	Yield
With 3-Methylpyridine; methanesulfonyl chloride In propiononitrile at -5 - 20℃; for 4h; Product distribution / selectivity;	97%
With 3-Methylpyridine; methanesulfonyl chloride In acetone at -5 - 5℃; for 3h; Product distribution / selectivity;	96.4%
With pyridine; methanesulfonyl chloride In acetonitrile at -5 - 20℃; for 4h; Product distribution / selectivity;	96.8%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: C9H6Br2ClN3O2

: C18H15Br2Cl2N5O2

Conditions

Conditions	Yield
With pyridine; methanesulfonyl chloride In acetonitrile at -5℃; for 2.16h;	95.6%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 67-64-1
acetone

: 1488427-93-5
6-chloro-2,2,3,8-tetramethyl-2,3-dihydroquinazolin-4(1H)-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 1h; Reflux;	95%

: 98-01-1
furfural

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 1542270-67-6
6-chloro-2-(furan-2-yl)-3,8-dimethyl-2,3-dihydroquinazolin-4(1H)-one

Conditions

Conditions	Yield
With β-cyclodextrine-SO3H In water at 50℃; for 0.416667h; Green chemistry;	94%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 1072138-63-6
3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxaldehyde

: 1351217-99-6
C18H14BrCl2N5O

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 1h; Reflux;	92%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 943982-60-3
3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride

: 500008-45-7
rynaxypyr

Conditions

Conditions	Yield
Stage #1: 2-amino-3-methyl-5-chlorobenzoyl-N-methylamine With 3-Methylpyridine In acetonitrile at 25 - 35℃; Stage #2: 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride In acetonitrile at 25 - 35℃; Solvent; Temperature;	91.1%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; Cooling with ice;	89.3%
Stage #1: 2-amino-3-methyl-5-chlorobenzoyl-N-methylamine; 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride In acetonitrile at 20℃; for 1.16667h; Reflux; Stage #2: With sodium hydrogencarbonate In acetonitrile Product distribution / selectivity;

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 108-94-1
cyclohexanone

: 1542270-66-5
6'-chloro-3',8'-dimethyl-1'H-spiro[cyclohexane-1,2'-quinazolin]-4'(3'H)-one

Conditions

Conditions	Yield
With β-cyclodextrine-SO3H In water at 50℃; for 0.416667h; Green chemistry;	90%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carbonyl chloride

: 500008-45-7
rynaxypyr

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 3.16667h; Reflux;	84%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 557-21-1
dicyanozinc

: 2-amino-3-methyl-5-cyanobenzoyl-N-methylamine

Conditions

Conditions	Yield
With zinc; bis(tri-tert-butylphosphine)palladium(0) In 1,4-dioxane for 11h; Product distribution / selectivity; Heating / reflux;	83%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 151-50-8
potassium cyanide

: 2-amino-3-methyl-5-cyanobenzoyl-N-methylamine

Conditions

Conditions	Yield
chloro(1-naphthyl)bis(triphenylphosphine)nickel(II); chloro(2-naphthalenyl)bis(triphenylphosphine)nickel In ethanol; xylene at 45℃; Product distribution / selectivity;	82.5%
With zinc; bis(tri-tert-butylphosphine)palladium(0); 18-crown-6 ether In 1,4-dioxane for 24h; Product distribution / selectivity; Heating / reflux;	65%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 1450664-91-1
C9H6ClN3O

: 1450664-92-2
6-chloro-2-(3-chloro-1-(pyridin-2-yl)-1H-pyrazol-5-yl)-3-cyclopropyl-8-methyl-2,3-dihydroquinazolin-4(1H)-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 1h; Reflux;	82%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 1-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

: 1104384-03-3
C19H13Cl3F3N5O2

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	81%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 1104384-31-7
1-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-1H-pyrazole-5-carbonyl chloride

: 1104384-07-7
C21H16Cl3N5O3

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	81%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: C8H3Cl3N4O

: N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-chloro-1-(6-chloropyrazin-2-yl)-1H-pyrazole-5-carboxamide

Conditions

Conditions	Yield
With triethylamine In acetonitrile	76%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 1-(6-chloropyrazin-2-yl)-3-bromo-1H-pyrazole-5-carbonyl chloride

: N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(6-chloropyrazin-2-yl)-1H-pyrazole-5-carboxamide

Conditions

Conditions	Yield
With triethylamine In acetonitrile	75%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: C12H7Cl2F2N3O2

: N5-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2-chloro-4,5-difluorophenyl)-N3-methyl-1H-pyrazole-3,5-dicarboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;	75%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: C12H7Cl2F3N2O2

: N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2-chloro-5-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃;	73.5%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 79-04-9
chloroacetyl chloride

: 1374598-54-5
5-chloro-2-(2-chloroacetamido)-N,3-dimethylbenzamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3.6h;	73%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: C10H3BrCl2F2N2O

: 3-bromo-N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(2-chloro-4,5-difluorophenyl)-1H-pyrazole-5-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h;	73%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: 1-(pyrazin-2-yl)-3-bromo-1H-pyrazole-5-formyl chloride

: N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-bromo-1-(pyrazin-2-yl)-1H-pyrazole-5-carboxamide

Conditions

Conditions	Yield
With triethylamine In acetonitrile	72%

: 890707-28-5
2-amino-3-methyl-5-chlorobenzoyl-N-methylamine

: C9H6Cl2N4O2

: N-(2-(methylcarbamoyl)-4-chloro-6-methylphenyl)-3-methoxyl-1-(6-chloropyrazin-2-yl)-1H-pyrazole-5-carboxamide

Conditions

Conditions	Yield
With triethylamine In acetonitrile	71%

2-Amino-5-chloro-N,3-dimethylbenzamide Specification

The 2-Amino-3-methyl-N-methylbenzamide, with CAS registry number 890707-28-5, has the systematic name of 2-amino-5-chloro-N,3-dimethyl-benzamide. Besides this, it is also called benzamide, 2-amino-5-chloro-N,3-dimethyl-. And the chemical formula of this chemical is C₉H₁₁ClN₂O.

Physical properties of 2-Amino-3-methyl-N-methylbenzamide: (1)ACD/LogP: 2.15; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.15; (4)ACD/LogD (pH 7.4): 2.15; (5)#H bond acceptors: 3; (6)#H bond donors: 3; (7)#Freely Rotating Bonds: 2; (8)Polar Surface Area: 55.12 Å²; (9)Index of Refraction: 1.586; (10)Molar Refractivity: 53.83 cm³; (11)Molar Volume: 160.2 cm³; (12)Polarizability: 21.34×10^-24cm³; (13)Surface Tension: 47 dyne/cm; (14)Density: 1.239 g/cm³; (15)Flash Point: 140.5 °C; (16)Enthalpy of Vaporization: 54.95 kJ/mol; (17)Boiling Point: 308.8 °C at 760 mmHg; (18)Vapour Pressure: 0.000666 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1cc(cc(c1N)C(=O)NC)Cl
(2)InChI: InChI=1/C9H11ClN2O/c1-5-3-6(10)4-7(8(5)11)9(13)12-2/h3-4H,11H2,1-2H3,(H,12,13)
(3)InChIKey: WOBVZGBINMTNKL-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C9H11ClN2O/c1-5-3-6(10)4-7(8(5)11)9(13)12-2/h3-4H,11H2,1-2H3,(H,12,13)
(5)Std. InChIKey: WOBVZGBINMTNKL-UHFFFAOYSA-N

Product Name

Bardoxolone

Synthetic route

2-Amino-5-chloro-N,3-dimethylbenzamide Specification

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