Sulfuric Acid → 1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 3,4-dihydronaphthalen-1(2H)-one (2.0 g, 13.68 mmol) and sodium azide (1.11 g, 17.10 mmol) in a mixture of 14 mL CHCl3 and 3 mL H2O was heated at 40° C. then treated with H2SO4 dropwise over 20 minutes. The mixture was diluted with 50 mL H2O and filtered. The solid was slurried in hot H2O, cooled and filtered to give a gray solid (1.45 g, 65.6%). 1H-NMR (DMSO-d6) δ 9.49 (s, 1H), 7.25-7.22 (m, 2H), 7.19-7.21 (m, 1H), 6.95 (d, J=7.8 Hz, 1H), 2.70-2.65 (m, 2H), 2.15-2.07 (m, 4H). MS (EI): 161 (M+).

Provenance & Evidence