4-Methylmorpholine → 3-Fluoro-4-nitrobenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-fluoro-4-nitrobenzoic acid, J. Am. Chem. Soc. 66, 1631-1632 (1944), (2.0 g, 10.81 mmol) in tetrahydrofuran (100 mL) at 0° C. was added 4-methyl morpholine (1.78 mL, 16.21 mmol), 1-hydroxybenzotriazole (2.18 g, 16.21 mmol), followed by 1-(3 dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.10 g, 16.21 mmol). The reaction was stirred for 1 hour at 0° C., then concentrated ammonium hydroxide was added (2.19 mL, 16.21 mmol). The reaction was allowed to warm slowly to room temperature and stirred overnight. The reaction was then diluted with ethyl acetate and washed with 5% citric acid (50 mL), saturated sodium bicarbonate (50 mL), and saturated sodium chloride (50 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield a pale yellow powder. The powder was collected and washed with ether, followed by drying under reduced pressure to yield 3-fluoro-4-nitro-benzamide 1.22 g (69%). MS(APCI) m/z 183.0 (M−H). Anal. Calcd. for C7H5N2O3F1: C, 45.66; H, 2.74; N, 15.21. Found: C, 46.03; H, 2.75; N, 15.02.

Provenance & Evidence