Dimethylamine, hydrochloride → 2-chloro-N,N-dimethyl-4-nitrobenzamide

Participants

Reaction Steps

2-chloro-4-nitrobenzoyl chloride Compound 13a1 (7.08 g, 32.2 mmol) and dimethylamine hydrochloride (2.62 g, 32.2 mmol) were combined in THF (50 mL) at 0° C. TEA (8.97 mL, 64.4 mmol) was added and the mixture was heated at reflux for 18 hrs. When the reaction was complete, the mixture was diluted with 1N HCl and extracted with EtOAc. The product was isolated by flash chromatography (30-50% EtOAc/hexane gradient) to provide 2-chloro-N,N-dimethyl-4-nitro-benzamide Compound 13a2 (3.05 g) as a tan solid. MS 229 (MH+).

Provenance & Evidence