Methylamine → 5-Fluoro-N-methyl-2-nitrobenzamide

Participants

Reaction Steps

A solution of 5-fluoro-2-nitrobenzoic acid (0.5 g, 2.7 mmol) in dichloromethane (10 mL) was cooled with an ice water bath before the addition of N,N-diisopropylethylamine (1.13 g, 8.1 mmol). To this solution 2M methylamine in tetrahydrofuran (1.6 g, 3.24 mmol) was added dropwise over 5 minutes. 1-Propanephosphonic acid cyclic anhydride as a 50% wt solution in ethyl acetate (2.56 mL, 4.05 mmol) was added dropwise. The ice bath was then removed and stirring continued overnight. The mixture was purified on a 2 g ABW column to afford 5-fluoro-N-methyl-2-nitrobenzamide (0.26 g, 1.31 mmol).

Provenance & Evidence