3-Ethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 3-Ethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine

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Reaction Steps

3-Ethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (740 mg/3.4 mmol) was dissolved in anhydrous methanol (ca. 10 mL) and the solution added to a Parr flask. Palladium (10% on charcoal) was added carefully (WARNING: this addition should be done under a atmosphere of nitrogen to avoid ignition of methanol vapor in flask) and the mixture shaken under 40 psi of hydrogen for 2 hours. The mixture was then filtered and the colorless filtrate concentrated to afford 3-Ethyl-2,3,4,5-tetrahydro-1H-benzo [d]azepin-7-ylamine (yellows upon standing). The material was typically used without further purification (680 mg/quantitative). 1H NMR (400 MHz, CDCl3) δ 6.9 (d, J=7.6 Hz, 1H), 6.4 (m, 2H), 2.9 (m, 4H), 2.7 (m, 6H), 1.1 (t, J=7.1 Hz, 3H).

Provenance & Evidence