Sulfuric Acid → N-tert-Butyl-3-methylpyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

111 g (1.5 mol) of tert.-butanol and 118 g (1 mol) of 3-methyl-2-cyanopyridine in 100 ml of glacial acetic acid are initially taken. 147 g of sulphuric acid (100% strength) are added dropwise to this mixture at 50° C. in the course of 0.5 hours, and the mixture is stirred for 3 hours at 50° C. The oil is stirred into 1,000 ml of water, and the resulting solution is adjusted to pH 7 with concentrated sodium hydroxide solution, while cooling with ice. The oil which separates out is separated off, taken up in methylene chloride and extracted by shaking with water. The organic phase is dried over sodium sulphate, evaporated down and distilled. 166.5 g (86.7% of theory) of 3-methylpyridine-2-carboxylic acid N-tert.-butylamide are obtained as a viscous oil of boiling point 155° C./4 mbar.

Provenance & Evidence