3-Pyridinecarboxylicacid,5,6-dimethyl-(9CI) synthesis
- Product Name:3-Pyridinecarboxylicacid,5,6-dimethyl-(9CI)
- CAS Number:757903-81-4
- Molecular formula:C8H9NO2
- Molecular Weight:151.16
113124-09-7
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757903-81-4
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Yield: 99%
Reaction Conditions:
Stage #1:5,6-dimethyl-3-pyridinecarbonitrile with water;sodium hydroxide in ethanol for 3 h;Reflux;
Stage #2: with hydrogenchloride in ethanol;water at 0;
Steps:
14.1 N-[4-(2-Furyl)-5-(tetrahydropyran-4-carbonyl)thiazol-2-yl]-5,6-dimethylpyridine-3-carboxamide (compound (IQ))
step 1 5,6-Dimethylpyridine-3-carbonitrile (502 mg, 3.79 mmol) obtained by the method described in J. Heterocyclic Chem., vol. 24, p. 351 (1987) was suspended in 70% aqueous ethanol (4.5 mL), sodium hydroxide (444 mg, 11.1 mmol) was added thereto, and the mixture was stirred with heating under reflux for 3 hr. The mixture was ice-cooled to 0°C, and 6 mol/L hydrochloric acid (1.9 mL) was added thereto. The mixture was concentrated under reduced pressure and the obtained residue was suspended in chloroform-methanol. The inorganic salt was removed by filtration, and the obtained filtrate was concentrated under reduced pressure to give 5,6-dimethylpyridine-3-carboxylic acid (569 mg, 99%) as a pale-pink solid. 1H NMR (DMSO-d6, δpam): 2.23 (s, 3H), 2.39 (s, 3H), 7.83 (d, J = 1.7 Hz, 1H), 8.64 (d, J = 1.7 Hz, 1H).
References:
Kyowa Hakko Kirin Co., Ltd. EP2474543, 2012, A1 Location in patent:Page/Page column 22
1174028-18-2
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41667-95-2
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