Nitric Acid → 3-acetyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Participants

Reaction Conditions

Reaction Steps

1-(1,2,4,5-Tetrahydrobenzo[d]azepin-3-yl)ethanone (3.8 g) was dissolved in a 2:1 mixture of acetic acid and 96% sulphuric acid (15 ml), then the mixture was cooled to 0° C. and a 3:2 mixture of 65% nitric acid and 96% sulphuric acid (2.5 ml) was added dropwise, while the temperature was maintained below 5° C. The mixture was stirred for additional 30 min, then poured into crushed ice (300 g) and extracted with ethyl acetate. The organic phase was washed with 5% aqueous NaHCO3, dried over Na2SO4 and concentrated to afford a crude material (4.3 g). Filtration through a silica gel pad (DCM/MeOH, 98/2) yielded the title compound as a yellow solid (4.0 g, 85% yield).

Provenance & Evidence