Nitric Acid → 7-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepine

Participants

Reaction Conditions

Reaction Steps

A solution of 2,3,4,5-tetrahydro-1H-benzo[d]azepine dissolved in conc. H2SO4 (1.5 mL) was cooled to 0° C. and a mixture of concentrated H2SO4 (0.12 mL) and fuming HNO3 (0.06 mL) (also cooled to 0° C.) was added dropwise. After the addition was complete, the mixture was stirred for 15-30 min. The reaction mixture was poured onto 10 g of crushed ice, followed by the dropwise addition of 20% NaOH solution. The mixture was extracted with EtOAc (3×). The organic layer was washed with H2O, dried (Na2SO4), concentrated and under vacuum to afford 7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a brown liquid (0.12 g, 46% yield). LC-MS (EI) m/z: 193.0 (M+H+).

Provenance & Evidence