2-Amino-4-methylpyridine → 2-chloro-N-(4-methylpyridin-2-yl)acetamide

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19]>CCOCC>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:18](=[O:19])[CH2:17][Cl:16])[CH:7]=1

Participants

Procedure

A solution of 2-amino-4-methylpyridine (10.8 grams) in ether (150 ml), and triethylamine (10 grams) are placed in a reaction flask equipped with stirrer, thermometer and addition funnel. The reaction mixture is cooled to a temperature of about 0° C and chloroacetyl chloride (11.3 grams) dissolved in ether (30 ml) is slowly added thereto resulting in the formation of a precipitate. Stirring is continued for a period of about 1 hour. After this time the reaction mixture is filtered to recover the precipitate that has formed. The precipitate is washed with aqueous potassium carbonate and with water. The washed precipitate is then dried to yield the desired product N-(4-methyl-2-pyridyl)-α-chloroacetamide.