Triethylamine → HCID 20081761, compound

Participants

Reaction Conditions

Reaction Steps

Dimethylaminopyridine (15 mg) followed by triethylamine (4.14 mL, 0.0279 mol) were added to a stirred solution of 2-amino-3-methylbenzoic acid (1.50 g, 0.0099 mol) in DMF (15 mL) under nitrogen at 0° C. The iso-butyryl chloride (2.07 mL, 0.0198 mol) was added dropwise then the mixture stirred at 0° C. for 30 min. followed by 30 min. at room temperature then at 120° C. for 1 hr. The suspension was then stirred at room temperature for 2 days. Ammonium carbonate (3.5 g) was added in portions and the mixture heated at 120° C. for 3 hr. After cooling to room temperature the mixture was poured into ice/water and extracted with ethyl acetate (3 times). The combined organic phase was washed with water, brine, dried (magnesium sulfate) and the solvent removed in vacuo to leave a cream solid. Recrystallisation (1:1 ethyl acetate/hexane) afforded 2-(iso-butyryl)amino-3-methylbenzamide (739 mg, 34%).

Provenance & Evidence