Aminoacetaldehyde dimethyl acetal → N-(2,2-dimethoxyethyl)-3-fluoro-4-nitro-benzamide

Participants

Reaction Steps

To a cooled solution of amino acetaldehyde dimethyl acetal (0.91 mL, 8.30 mmol) in dry tetrahydrofuran (15 mL) was added sodium bicarbonate (769 mg, 9.16 mmol) and then a solution of 3-fluoro-4-nitro-benzoyl chloride (1.7 g, 8.30 mmol) in dry tetrahydrofuran (15 mL) was added dropwise at 0° C. over a period of 30 min. The reaction mixture was stirred overnight at ambient temperature, the solvent was removed in vacuo, and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated to yield N-(2,2-dimethoxyethyl)-3-fluoro-4-nitro-benzamide (2.0 g, 90%) as a brown liquid.

Provenance & Evidence