3-Chloro-2-nitrobenzoic acid → HCID 11221793, compound

Participants

Reaction Steps

To a suspension of 3-chloro-2-nitrobenzoic acid (2.68 g) in dichloromethane (10 ml) at 0° C. was added oxalyl chloride (3 ml) and dimethylformamide (1 drop). The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour, then concentrated under reduced pressure to yield a solid. The solid was dissolved in dichloromethane (10 ml) and cooled to 0° C. A solution of 1-adamantanemethylamine (2.19 g) and N,N-diisopropylethylamine (11 ml) in dichloromethane (10 ml) was added portion-wise and the resulting solution allowed to stir at room temperature under a nitrogen atmosphere for 2 h. The reaction mixture was poured into water and the organic phase separated and washed with 2N hydrochloric acid, 10% aqueous sodium hydroxide and saturated brine. The organic phase was then dried over sodium sulfate, filtered and concentrated under reduced pressure and the resulting solid recrystallized from iso-propanol to afford the subtitle compound as a solid (3.52 g).

Provenance & Evidence