Ammonia → N-tert-Butyl-3-methylpyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-cyano-3-methyl pyridine (400 g) is suspended in t-butyl alcohol (800 mL) and the mixture heated to 70° C. Concentrated sulphuric acid (400 mL) is added dropwise over 45 minutes. The reaction is complete after a further 30 minutes at 75° C. The mixture is then diluted with water (400 mL), charged with toluene (600 mL) and brought to pH 10 with concentrated aqueous ammonia. The temperature is kept at 50-55° C. during the work up. The toluene phase is separated, the aqueous layer re-extracted and the combined toluene phases are washed with water. Removal of the toluene yields an oil from which solid product may crystallize. Product yield of 97% determined by internal standard assay on gas chromatograph.

Provenance & Evidence