Conditions | Yield |
---|---|
100% |
Conditions | Yield |
---|---|
With potassium permanganate In water at 80℃; for 0.05h; | 84.2% |
With potassium hydroxide; potassium permanganate In water; acetone at 30℃; for 2h; Title compound not separated from byproducts; |
1-(6-methyl-pyridin-3-yl)-ethanone
6-methylnicotinic acid
Conditions | Yield |
---|---|
With nitric acid for 5h; Heating; | 75.4% |
With nitric acid |
2,5-dimethylpyridine
A
6-methylnicotinic acid
B
Pyridine-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With potassium permanganate In water at 90℃; for 6.2h; | A 14.5% B 70.8% |
With potassium permanganate In water at 80℃; for 1.5h; Product distribution; other pyridines, var. temp.; | A 47.1% B 12.3% |
5-ethyl-2-methyl-pyridine
A
6-methylnicotinic acid
B
5-ethylpyridine-2-carboxylic acid
C
Pyridine-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With potassium permanganate In water at 90℃; for 0.433333h; | A 57.5% B 3.5% C 18.4% |
With potassium permanganate In water at 80℃; for 0.166667h; | A 42% B 5.4% C 1.6% |
2,5-dimethylpyridine
A
2-carboxy-5-methylpyridine
B
6-methylnicotinic acid
C
Pyridine-2,5-dicarboxylic acid
Conditions | Yield |
---|---|
With potassium permanganate In water at 80℃; for 1.5h; | A 19.1% B 47.1% C 12.3% |
Conditions | Yield |
---|---|
With selenium(IV) oxide; nitric acid | |
With potassium permanganate at 60℃; | |
With potassium permanganate; water | |
With nitric acid; vanadia |
Conditions | Yield |
---|---|
With sulfuric acid |
ethyl 6-methylnicotinate
6-methylnicotinic acid
Conditions | Yield |
---|---|
With potassium hydroxide | |
With hydrogenchloride In water at 80℃; | |
With lithium aluminium tetrahydride In tetrahydrofuran |
Conditions | Yield |
---|---|
Erhitzen auf Siedetemperatur; |
Conditions | Yield |
---|---|
With water In acetonitrile at 37℃; for 0.166667h; pH=2.0; Kinetics; Further Variations:; pH-values; reaction time; Acid hydrolysis; |
5-Amino-2-methylpyridine
6-methylnicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous CuSO4 / Diazotization 2: aqueous H2SO4 View Scheme |
ethyl 2,4-dichloro-6-methylpyridine-3-carboxylate
6-methylnicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: palladium; potassium acetate; ethanol / Hydrogenation 2: aqueous KOH View Scheme |
ethyl 2,4-dihydroxy-6-methylnicotinate
6-methylnicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: POCl3 / 130 °C 2: palladium; potassium acetate; ethanol / Hydrogenation 3: aqueous KOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: fluorosulfonyl fluoride; triethylamine / dichloromethane / 24 h / 20 °C / 760.05 Torr 2: bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline; manganese / N,N-dimethyl-formamide / 20 h / 20 °C / 760.05 Torr / Schlenk technique; Inert atmosphere; Glovebox View Scheme |
Conditions | Yield |
---|---|
With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox; |
6-methylnicotinic acid
glyoxylic acid ethyl ester
6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]nicotinic acid
Conditions | Yield |
---|---|
With acetic anhydride In toluene at 20 - 130℃; for 20h; | 100% |
6-methylnicotinic acid
acide methyl-6 nipecotique
Conditions | Yield |
---|---|
With ammonia; hydrogen; 5% rhodium on alumina In water under 2068.65 Torr; for 72h; | 100% |
6-methylnicotinic acid
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 70℃; for 13h; | 100% |
2,3-Diaminopyridine
6-methylnicotinic acid
2-(6-Methyl-pyridin-3-yl)-1H-imidazo[4,5-b]pyridine
Conditions | Yield |
---|---|
With PPA at 210℃; for 2h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 6-methylnicotinic acid With 1,1'-carbonyldiimidazole In ethyl acetate for 5h; Reflux; Stage #2: tryptamine In ethyl acetate for 12h; Reflux; | 98% |
2-amino-3-hydroxypyridine
6-methylnicotinic acid
2-(6-Methyl-pyridin-3-yl)-oxazolo[4,5-b]pyridine
Conditions | Yield |
---|---|
With PPA at 210℃; for 2h; | 96% |
6-methylnicotinic acid
Conditions | Yield |
---|---|
In dichloromethane under N2; suspn. of (Cu(dppm)MeCN))2(BF4)2 and 6-methyl-3-pyridinecarboxylic acid in CH2Cl2 was stirred at ambient temp. for 30 min, resulting soln. was stirred for 10 min; evapn. under vac., ppt. was washed with Et2O, recrystn. from CH2Cl2/hexane; elem. anal.; | 96% |
6-methylnicotinic acid
N,O-dimethylhydroxylamine*hydrochloride
N-methoxy-N-methyl-6-methylnicotinamide
Conditions | Yield |
---|---|
Stage #1: 6-methylnicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With pyridine In dichloromethane at 0 - 20℃; for 18h; | 95% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; | 91% |
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 23℃; | 90% |
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran; methanol at 20℃; for 3h; | 82% |
Stage #1: 6-methylnicotinic acid With pivaloyl chloride In dichloromethane at 0℃; for 1h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃; for 2.5h; | 51% |
6-methylnicotinic acid
(S)-3-[3-(trimethylsilanyl)prop-2-ynyl]morpholine
(6-methylpyridin-3-yl)-{(S)-[3-(trimethylsilanyl)prop-2-ynyl]morpholin-4-yl}-methanone
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 16h; | 93% |
6-methylnicotinic acid
[(S)-3-(5-benzyloxy-1-methyl-1H-indol-3-ylmethyl)morpholine-4-yl]-(6-methylpyridin-3-yl)-methanone
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; | 93% |
6-methylnicotinic acid
D-threoninol
N-(2-hydroxy-1-hydroxymethylpropyl)-6-methyl-nicotinamide
Conditions | Yield |
---|---|
Stage #1: 6-methylnicotinic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: D-threoninol In N,N-dimethyl-formamide at 20℃; | 92% |
6-methylnicotinic acid
(3R)-1-[bis-(4-chlorophenyl)methyl]-3-aminopyrrolidine
Conditions | Yield |
---|---|
Stage #1: 6-methylnicotinic acid; (3R)-1-[bis-(4-chlorophenyl)methyl]-3-aminopyrrolidine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide); chloroform at 20℃; Stage #2: With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide); chloroform; water for 0.25h; | 92% |
6-methylnicotinic acid
4-fluoroaniline
N-(4-fluorophenyl)-6-methylnicotinamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux; | 92% |
6-methylnicotinic acid
3-aminophenylboronic acid pinacolate
Conditions | Yield |
---|---|
Stage #1: 6-methylnicotinic acid; 3-aminophenylboronic acid pinacolate With HATU In N,N-dimethyl-formamide at 30℃; for 0.0833333h; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 30℃; for 16h; | 92% |
Conditions | Yield |
---|---|
Stage #1: 6-methylnicotinic acid With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: benzyl bromide In tetrahydrofuran at 20℃; for 48h; | 92% |
Conditions | Yield |
---|---|
With dmap In toluene Concentration; Reflux; | 91.9% |
6-methylnicotinic acid
tert-butyl alcohol
tert-butyl N-(6-methylpyridin-3-yl)carbamate
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; triethylamine In 1,4-dioxane at 20℃; for 18h; Product distribution / selectivity; Heating / reflux; | 88% |
With diphenyl phosphoryl azide; triethylamine In 1,4-dioxane at 20℃; for 18h; Heating / reflux; | 88% |
With diphenyl phosphoryl azide; triethylamine for 19h; Product distribution / selectivity; Heating / reflux; | 87% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.166667h; | 88% |
6-methylnicotinic acid
Conditions | Yield |
---|---|
Stage #1: 6-methylnicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 1h; Stage #2: tert-butyl 3-(3-amino-5-chloro-2-methylbenzyl)-3,8-diazabicyclo[3.2.1]octan-8-carboxylate With triethylamine In dichloromethane at 0 - 20℃; | 87.5% |
6-methylnicotinic acid
(S)-N-[1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine
N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)-6-methylnicotinamide
Conditions | Yield |
---|---|
With 4-pyrrolidin-1-ylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 72h; | 86% |
With 4-pyrrolidin-1-ylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 48h; |
6-methylnicotinic acid
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 60℃; for 2h; | 86% |
4-(2-AMINOETHYL)MORPHOLINE
6-methylnicotinic acid
6-methyl-N-(2-morpholinoethyl)nicotinamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux; | 85% |
6-methylnicotinic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 85% |
6-methylnicotinic acid
Conditions | Yield |
---|---|
Stage #1: 6-methylnicotinic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: 4-(aminomethyl)-1-methyl-5,6,7,8-tetrahydroisoquinolin-3(2H)-one In dichloromethane at 20℃; for 7h; | 85% |
6-methylnicotinic acid
1-[2'-(hydroxy)ethyl]-2-ethyl-3-benzyloxy-4(1H)-pyridinone
6-methyl-nicotinic acid 2-(3-benzyloxy-2-ethyl-4-oxo-4H-pyridin-1-yl)-ethyl ester
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Esterification; | 81% |
6-methylnicotinic acid
4-[[3-[[5-(trifluoromethyl)-2-pyridyl]oxy]phenyl]methylene]-cyclohexanamine
6-methyl-N-[4-[[3-[[5-(trifluoromethyl)-2-pyridyl]oxy]phenyl]-methylene]cyclohexyl]pyridine-3-carboxamide
Conditions | Yield |
---|---|
Stage #1: 6-methylnicotinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 4-[[3-[[5-(trifluoromethyl)-2-pyridyl]oxy]phenyl]methylene]-cyclohexanamine With 4-methyl-morpholine In N,N-dimethyl-formamide for 18h; | 81% |
Stage #1: 6-methylnicotinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 4-[[3-[[5-(trifluoromethyl)-2-pyridyl]oxy]phenyl]methylene]-cyclohexanamine With 4-methyl-morpholine In N,N-dimethyl-formamide for 18h; | 81% |
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 80% |
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.166667h; | 80% |
The 6-Methylnicotinic acid is an organic compound with the formula C7H7NO2. The IUPAC name of this chemical is 6-methylpyridine-3-carboxylic acid. With the CAS registry number 3222-47-7, it is also named as 3-Pyridinecarboxylic acid, 6-methyl-. The product's categories are Acids and Derivatives; Heterocycles; Pharmacetical; Pyridine; Organic Acids. Besides, it is a white crystalline, which should be stored in a cool dry and well-ventilated area away from incompatible substances.
Physical properties about 6-Methylnicotinic acid are: (1)ACD/LogP: 0.61 ; (2)ACD/LogD (pH 5.5): -1.41; (3)ACD/LogD (pH 7.4): -2.43; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 39.19 Å2; (12)Index of Refraction: 1.561; (13)Molar Refractivity: 36.09 cm3; (14)Molar Volume: 111.4 cm3; (15)Polarizability: 14.31×10-24cm3; (16)Surface Tension: 53.3 dyne/cm; (17)Density: 1.23 g/cm3; (18)Flash Point: 132.9 °C; (19)Enthalpy of Vaporization: 56.6 kJ/mol; (20)Boiling Point: 296.2 °C at 760 mmHg; (21)Vapour Pressure: 0.000659 mmHg at 25°C.
Preparation: this chemical can be prepared by 1-(6-methyl-pyridin-3-yl)-ethanone. This reaction will need reagent nitric acid.
Uses of 6-Methylnicotinic acid: it can be used to produce 2-(6-methyl-pyridin-3-yl)-1H-imidazo[4,5-b]pyridine at temperature of 210 °C. It will need reagent polyphosphoric acid with reaction time of 2 hours. The yield is about 98%.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)c1cnc(cc1)C
(2)InChI: InChI=1/C7H7NO2/c1-5-2-3-6(4-8-5)7(9)10/h2-4H,1H3,(H,9,10)
(3)InChIKey: RZOKQIPOABEQAM-UHFFFAOYAJ
(4)Std. InChI: InChI=1S/C7H7NO2/c1-5-2-3-6(4-8-5)7(9)10/h2-4H,1H3,(H,9,10)
(5)Std. InChIKey: RZOKQIPOABEQAM-UHFFFAOYSA-N
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