ChemicalBook CAS DataBase List 6-Chloro-N,N-dimethyl-3-pyridinecarboxamide

6-Chloro-N,N-dimethyl-3-pyridinecarboxamide synthesis

4synthesis methods

Product Name:6-Chloro-N,N-dimethyl-3-pyridinecarboxamide
CAS Number:54864-83-4
Molecular formula:C8H9ClN2O
Molecular Weight:184.62

70258-18-3 Synthesis

70258-18-3
501 suppliers
$5.00/5g

124-40-3
499 suppliers
$18.00/100ml

6-Chloro-N,N-dimethyl-3-pyridinecarboxamide

54864-83-4
70 suppliers
$5.00/100mg

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

5326-23-8 Synthesis