6-Chloro-N,N-dimethyl-3-pyridinecarboxamide synthesis
- Product Name:6-Chloro-N,N-dimethyl-3-pyridinecarboxamide
- CAS Number:54864-83-4
- Molecular formula:C8H9ClN2O
- Molecular Weight:184.62
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Yield: 97%
Reaction Conditions:
in tetrahydrofuran;dichloromethane at 0 - 20;
Steps:
51.1
A tetrahydrofuran solution (14.2 ml, 28.4 mmol) of 2M-N,N-dimethylamine was added to a methylene chloride solution (17 ml) of 6-chloronicotinyl chloride (1.00 g, 5.68 mmol), at 0°C, and stirring was carried out at room temperature overnight. The reaction solution was concentrated and the resulting residue was diluted with methylene chloride, followed by sequential washing with water and saline, and the resulting organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated and the resulting residue was purified by silica gel column chromatography to afford 6-chloro-N,N-dimethylnicotinamide (1.02 g, yield 97%) as a pale red oil. 1H-NMR (CDCl3, 400 MHz) δ: 8.47 (1H, d, J=2.4 Hz), 7.75 (1H, dd, J=8.2 Hz, 2.4 Hz), 7.40 (1H, d, J=8.2 Hz), 3.13 (3H, s), 3.03 (3H, s). MS (ESI, m/z): 185 (M+H)+.
References:
Daiichi Sankyo Company, Limited EP2258697, 2010, A1 Location in patent:Page/Page column 72
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