Acetic Acid → Ethyl 5-amino-2-fluorocarbanilate

Participants

Reaction Conditions

Reaction Steps

A mixture of 39.4 g (706 mmol) of iron powder and 75 ml of an aqueous solution of 5% acetic acid was heated to 80° C., and a mixed solution of 16.1 g (70.6 mmol) of ethyl 2-fluoro-5-nitrocarbanilate, 72 ml of acetic acid and 72 ml of ethyl acetate was slowly added dropwise to the mixture. After the reaction was continued for 3 hours, the insolubles were filtered out and washed with ethyl acetate. Thereafter the filtrate was distilled to remove the solvent, and the resultant product was dissolved in ethyl acetate and washed with saturated sodium hydrogencarbonate, water and saturated saline solution. The solution was dried over anhydrous sodium sulfate, and the ethyl acetate was distilled off to obtain the crude product (crystals). The crude product was washed with diisopropyl ether, thereby obtaining 12.8 g of the objective product (yield: 91%) in the form of light yellow crystals.

Provenance & Evidence