4-Nitrobenzoyl chloride → HCID 4148717, compound

Participants

Reaction Steps

A solution of 18.9 g of 4-nitrobenzoyl chloride in 100 ml of tetrahydrofuran was added rapidly to a solution of 10.0 g of 1,2,3,4-tetrahydro-1-naphthylamine in 200 ml of tetrahydrofuran and 180 ml of 20% aqueous potassium carbonate. The reaction mixture was stirred vigorously and heated at reflux for 2 hours. After cooling, the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic portions were washed with water, 1N hydrochloric acid, water, and a saturated sodium chloride solution, dried over sodium sulfate, and concentrated in vacuo. The resulting solid was recrystallized from benzene to afford the title intermediate in 90% yield as a colorless solid, m.p. 156°-157° C.

Provenance & Evidence