Chloroform → N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

Participants

Reaction Steps

A solution of N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide (16.2 g) in acetic acid (200 ml) is dropwise added to a suspension of iron powder (14 g) in a 5% aqueous acetic acid (30 ml) at 90°-100° C. and refluxed for 1 hour. After being allowed to cool, chloroform is added to the resultant mixture, followed by filtration. The organic layer is separated from the filtrate, washed with a saturated sodium hydrogen carbonate solution, dried and concentrated. The residue is recrystallized from a mixture of ether and petroleum ether to give 7.5 g of N-(3-amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide. M.P., 144.5°-146.5° C.

Provenance & Evidence