1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid supplier

Name
1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid
EINECS
CAS No. 3719-45-7
Article Data27
CAS DataBase
Density 1.382 g/cm³
Solubility
Melting Point 240-245°C
Formula C₇H₇NO₃
Boiling Point 329.6 °C at 760 mmHg
Molecular Weight 153.137
Flash Point 153.2 °C
Transport Information
Appearance
Safety 26-36/37
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Nudifloric acid;Nicotinicacid, 1,6-dihydro-1-methyl-6-oxo- (6CI,7CI,8CI);1-Methyl-6-pyridone-3-carboxylic acid;1-Methylpyridin-2-one-5-carboxylic acid;
PSA 59.30000
LogP 0.08350

Synthetic route

: 6375-89-9
methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
With water; sodium hydroxide In tetrahydrofuran at 35℃; for 3h;	99%
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 3h;	80%
With water; sodium hydroxide In tetrahydrofuran at 20℃;	80%

: 77837-12-8
1,6-dihydro-6-imino-1-methyl-3-pyridinecarboxamide

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide for 4h; Heating;	90%

: 5006-66-6
6-hydroxy-3-pyridinecarboxylic acid

: 74-88-4
methyl iodide

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 6-hydroxy-3-pyridinecarboxylic acid With sodium hydride In methanol at 20 - 60℃; for 0.583333h; Inert atmosphere; Stage #2: methyl iodide In methanol at 60℃; Stage #3: With hydrogenchloride; sodium hydroxide In methanol; water at 60℃;	69%
With potassium hydroxide In methanol; water for 12h; Reflux; Inert atmosphere;	63%
With alkali
With sodium methylate for 3h; Heating;

: 13441-42-4
1-methylpyridinium-3-carb(ox)aldehyde

A: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

B: 98279-50-6
1-methyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde

Conditions

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III)	A n/a B 30%

: 3-(Carboxymethyl)-1-methylpyridiniumiodid

A: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

B: 98279-50-6
1-methyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde

C: 2-(1-methyl-6-oxo-1,6-d ihydropyridin-3-yl)acetic acid

D: 1,2-Dihydro-1-methyl-2-oxo-3-pyridinessigsaeure

Conditions

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III) for 2h;	A 3% B 1.3% C 3.9% D 22%

...Expand

: 3-(Carboxymethyl)-1-methylpyridiniumiodid

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III)	10%

: 59-67-6
nicotinic acid

: 67-56-1
methanol

: 77-78-1
dimethyl sulfate

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
Behandeln des Reaktionsprodukts mit K3 und wss. NaOH;

...Expand

: 5006-66-6
6-hydroxy-3-pyridinecarboxylic acid

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide durch Eindampfen und Erhitzen des Produkts mit Methyljodid und Methanol auf 100grad bis 110grad;
Multi-step reaction with 3 steps 1: sulfuric acid / 3 h / 65 - 70 °C 2: potassium carbonate / N,N-dimethyl-formamide / 72 h / 95 °C 3: sodium hydroxide; water / tetrahydrofuran / 3 h / 35 °C View Scheme

: 5326-23-8
6-Chloro-3-pyridinecarboxylic acid

: 77-78-1
dimethyl sulfate

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
Erhitzen des Reaktionsgemisches mit wss. NaOH;

: 1126-42-7
5-acetyl-1,2-dihydro-1-methyl-2(1H)-pyridone

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hypobromide

: 6018-41-3
methyl coumalate

: 74-89-5
methylamine

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 6375-89-9
methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

A: 67-56-1
methanol

B: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
With potassium chloride In water at 25℃; Rate constant;

3-carboxy-1-methyl-pyridinium-hydrogen sulfate: 3-carboxy-1-methyl-pyridinium-hydrogen sulfate

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III)

: 535-83-1
Trigonelline

aqueous H2O2: aqueous H2O2

aq.-ethanolic NaOH: aq.-ethanolic NaOH

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

...Expand

: 535-83-1
Trigonelline

potassium hexacyanoferrate(III): potassium hexacyanoferrate(III)

aqueous NaOH: aqueous NaOH

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

...Expand

: 74-88-4
methyl iodide

A: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

B: 6375-89-9
methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Conditions

Conditions	Yield
Stage #1: 6-hydroxy-3-pyridinecarboxylic acid With sodium hydride In methanol at 62℃; Stage #2: methyl iodide In methanol

: 6456-44-6
N-methylnicotineamide iodide

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / potassium permanganate, NH3(l) / 4 h / -33 °C 2: 90 percent / aq. KOH / 4 h / Heating View Scheme

: 55676-25-0
3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: anschliessendes Behandeln mit K3 2: water; hydrochloric acid 3: aqueous NaOBr View Scheme

: 162330-26-9
1,2-dihydro-5-<(ethylenedioxy)-ethyl>-1-methyl-2(1H)-pyridone

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water; hydrochloric acid 2: aqueous NaOBr View Scheme

: 66171-50-4
methyl 6-hydroxynicotinate

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 72 h / 95 °C 2: sodium hydroxide; water / tetrahydrofuran / 3 h / 35 °C View Scheme

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: (1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphth[1,2-e]indol-10-ol

: 5-((1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-10-hydroxy-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphth[1,2-e]indole-3-carbonyl)-1-methylpyridine-2(1H)-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 1h;	75%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 1172068-36-8
5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylamine

: 1196507-90-0
N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid; 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylamine With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 1h; Stage #2: With lithium hydroxide In dichloromethane for 0.5h;	69%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 3-chloro-N-((6-chloropyridin-3-yl)methyl)aniline

: N-(5-((3-chlorophenylamino)methyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 5h; Inert atmosphere;	67%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 2368-80-1
2-fluorophenylhydrazine

: N’-(2-fluorophenyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carbohydrazide

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-fluorophenylhydrazine With dmap In tetrahydrofuran at 20℃; for 2h;	65%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 6610-29-3
4-methylthiosemicarbazide

: 1-methyl-5-(4-methyl-5-sulfanyl-4H-1,2,4-triazol-3-yl)-1,2-dihydropyridin-2-one

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃;	65%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid; 4-methylthiosemicarbazide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃; Stage #2: With sodium hydroxide In ethyl acetate; N,N-dimethyl-formamide at 70℃;
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid; 4-methylthiosemicarbazide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling with ice; Stage #2: With sodium hydroxide In ethyl acetate; N,N-dimethyl-formamide at 70℃; for 0.666667h; pH=8 - 11; Inert atmosphere; Stage #3: With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide pH=5; Inert atmosphere;

: 100-42-5
styrene

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: C22H19NO

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In toluene at 160℃; for 24h; Molecular sieve; Inert atmosphere;	60%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 5-((1,3-dihydroisobenzofuran-5-yl)methyl)pyridin-2-amine

: N-(5-((1,3-dihydroisobenzofuran-5-yl)methyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 0.5h; Inert atmosphere; Stage #2: 5-((1,3-dihydroisobenzofuran-5-yl)methyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 0.2℃; for 2h;	55.3%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 0.5h; Inert atmosphere; Stage #2: 5-((1,3-dihydroisobenzofuran-5-yl)methyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 20℃; for 2h;	55.3%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 884497-40-9
5-(3-fluorobenzyl)-2-thiazolamine

: N-(5-(3-fluorobenzyl)thiazol-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;	54.6%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h;	54.6%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 5-(4-(trifluoromethyl)benzyl)pyridin-2-amine

: 1-methyl-6-oxo-N-(5-(4-(trifluoromethyl)benzyl)pyridin-2-yl)-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 0.5h; Inert atmosphere; Stage #2: 5-(4-(trifluoromethyl)benzyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 20℃; for 2h;	50.5%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 0.5h; Inert atmosphere; Stage #2: 5-(4-(trifluoromethyl)benzyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 20℃; for 2h;	50.5%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 3-((6-aminopyridin-3-yl)methyl)benzonitrile

: N-(5-(3-cyanobenzyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 85℃; for 1h; Stage #2: 3-((6-aminopyridin-3-yl)methyl)benzonitrile With pyridine In dichloromethane at 0 - 0.2℃; for 2h;	46%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 85℃; for 1h; Stage #2: 3-((6-aminopyridin-3-yl)methyl)benzonitrile With pyridine In dichloromethane at 0 - 20℃; for 2h;	46%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 19335-11-6
1H-indazol-5-ylamine

: N-(1H-Indazol-5-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;	45%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 1318757-72-0
tert-butyl [2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate

: 1318756-56-7
N-[2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: tert-butyl [2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate With hydrogenchloride In ethanol; water at 50℃; for 3h; Stage #2: With sodium hydrogencarbonate In ethanol; water Stage #3: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl acetamide at 0 - 60℃; for 6h;	44%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 91477-84-8
4-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine

: 1-methyl-5-(4-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5-carbonyl)pyridin-2(1H)-one

Conditions

Conditions	Yield
Stage #1: 4-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	43%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 5-[(3-fluorophenyl)methyl]pyridin-2-amine

: N-(5-(3-fluorobenzyl)pyridin-2-yl)-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: 5-[(3-fluorophenyl)methyl]pyridin-2-amine In tetrahydrofuran at 20℃; for 4h;	41%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 3066-71-5
cyclohexyl acrylate

A: cyclohexyl 2-(5-methyl-3,6-dioxo-1,3,5,6-tetrahydrofuro[3,4-c]pyridin-1-yl)acetate

B: cyclohexyl 2-(1-methyl-2,5-dioxo-1,2,5,7-tetrahydrofuro[3,4-b]pyridin-7-yl)acetate

C: dicyclohexyl 3,3'-(1-methyl-6-oxo-1,6-dihydropyridine-2,4-diyl)(2E,2'E)-diacrylate

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In toluene at 160℃; for 24h; Molecular sieve; Inert atmosphere;	A 10% B 5% C 40%

...Expand

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 5-(3-chloro-5-methoxybenzyl)pyridin-2-amine

: N-(5-(3-chloro-5-methoxybenzyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 1h; Stage #2: 5-(3-chloro-5-methoxybenzyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 20℃; for 2h;	38.6%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; Stage #2: 5-(3-chloro-5-methoxybenzyl)pyridin-2-amine In dichloromethane at 0 - 20℃; for 2h;	38.6%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 5-(4-fluorobenzyl)pyridin-2-amine

: N-(5-(4-fluorobenzyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With pyridine; trichlorophosphate at 0 - 20℃;	38.4%
With pyridine; trichlorophosphate at 20℃;	38.4%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: N2-benzyl-6-(4-methyl-piperazin-1-yl)-pyridine-2,3-diamine

: 5-[3-benzyl-5-(4-methyl-piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl]-1-methyl-1H-pyridin-2-one

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: N2-benzyl-6-(4-methyl-piperazin-1-yl)-pyridine-2,3-diamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #3: With acetic acid at 120℃; for 48h;	30%
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 1 h / 20 °C 2.1: acetic acid / 48 h / 120 °C View Scheme

Yield

Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: N2-benzyl-6-(4-methyl-piperazin-1-yl)-pyridine-2,3-diamine In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #3: With acetic acid at 120℃; for 48h;

30%

Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.08 h / 20 °C
1.2: 1 h / 20 °C
2.1: acetic acid / 48 h / 120 °C
View Scheme

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 5-(cyclohexylmethyl)pyridin-2-amine

: N-(5-(cyclohexylmethyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride In dichloromethane at 90℃; for 0.5h; Reflux; Stage #2: 5-(cyclohexylmethyl)pyridin-2-amine With pyridine In dichloromethane at 20℃; for 2h;	30%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride In dichloromethane at 20 - 90℃; for 0.5h; Stage #2: 5-(cyclohexylmethyl)pyridin-2-amine With pyridine In dichloromethane	30%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 823-85-8
4-fluorophenyhydrazine hydrochloride

: 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid N'-(4-fluorophenyl)hydrazide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;	29%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 4-(3-fluorobenzyl)aniline

: N-(4-(3-fluorobenzyl)phenyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With pyridine; trichlorophosphate at 20℃; for 1h;	27%
With pyridine; trichlorophosphate at 20℃; for 1h;	27%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 3-chloro-6-(3-chlorobenzyl)pyridazine

: N-(6-(3-chlorobenzyl)pyridazin-3-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 3h; Inert atmosphere;	26.9%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 1448440-51-4
(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile hydrochloride

: (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;	21%

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 5-(3-fluorophenoxy)pyridin-2-amine

: N-[5-(3-fluorophenoxy)pyridin-2-yl]-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU at 25℃; for 16h;	21%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 25℃; for 16h;	27.7 mg

: 3719-45-7
1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

: 4-(((3-ethoxy-4-isopropoxyphenyl)hydrazinocarbonylmethyl)amino)benzamidine dihydrochloride

: 76-05-1
trifluoroacetic acid

: 883574-25-2
4-(1-(3-ethoxy-4-isopropoxyphenyl)-2-(N'-(1-methyl-6-oxo-1,6-dihydropyridine-3-carbonyl)hydrazino)-2-oxoethylamino)benzamidine trifluoroacetate

Conditions

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide at 0℃; Stage #2: 4-(((3-ethoxy-4-isopropoxyphenyl)hydrazinocarbonylmethyl)amino)benzamidine dihydrochloride With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 72h; Stage #3: trifluoroacetic acid In water; acetonitrile	20%

Yield

Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide at 0℃;
Stage #2: 4-(((3-ethoxy-4-isopropoxyphenyl)hydrazinocarbonylmethyl)amino)benzamidine dihydrochloride With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 72h;
Stage #3: trifluoroacetic acid In water; acetonitrile

20%

...Expand

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid Specification

The 3-Pyridinecarboxylicacid, 1,6-dihydro-1-methyl-6-oxo-, with the CAS registry number 3719-45-7, has the systematic name and IUPAC name of 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid. And the molecular formula of the chemical is C₇H₇NO₃.

The characteristics of 3-Pyridinecarboxylicacid, 1,6-dihydro-1-methyl-6-oxo- are as followings: (1)ACD/LogP: -0.45; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.51; (4)ACD/LogD (pH 7.4): -3.99; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 46.61 Å²; (13)Index of Refraction: 1.577; (14)Molar Refractivity: 36.77 cm³; (15)Molar Volume: 110.8 cm³; (16)Polarizability: 14.57×10^-24cm³; (17)Surface Tension: 58 dyne/cm; (18)Density: 1.381 g/cm³; (19)Flash Point: 153.2 °C; (20)Enthalpy of Vaporization: 62.89 kJ/mol; (21)Boiling Point: 329.6 °C at 760 mmHg; (22)Vapour Pressure: 3.44E-05 mmHg at 25°C.

Uses of 3-Pyridinecarboxylicacid, 1,6-dihydro-1-methyl-6-oxo-: It can be used to produce 1,6-dihydro-6-imino-1-methyl-3-pyridinecarboxamide. This reaction will need reagent aq. KOH. The reaction time is 4 hours with heating, and the yield is about 90%.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C1/C=C\C(\C(=O)O)=C/N1C
(2)InChI: InChI=1/C7H7NO3/c1-8-4-5(7(10)11)2-3-6(8)9/h2-4H,1H3,(H,10,11)
(3)InChIKey: RGZCKPXTNJAWMR-UHFFFAOYAD

Product Name

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Synthetic route

1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid Specification

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