Ammonia → HCID 19027061, compound

Participants

Reaction Steps

A solution of 8-acetyl-1,2,3,4-tetrahydro-5-methoxy-6-nitronaphthalene (1.0 g, 4 mmol) in 15 ml of dry dimethylsulfoxide was heated to 100° C. and ammonia was passed into the solution for 3 h. After the solution was added to 100 ml of ice-water, the crude solid was filtered off and washed with water. Recrystallization from ethanol afforded 0.71 g (7 5%) of the pure title compound. M.p. 170°-172° C.; 1H-NMR (DMSO-d6): 1.47-1.93 (m, 4H, 2CH2), 2.27-2.63 (m, 2H, CH2), 2.48 (s, 3H, COCH3), 2.70-3.03 (m, 2H, CH2), 7.50 (broad s, 2H, NH2), 8.33 (s, 1H, H-7).

Provenance & Evidence