Sodium Hydroxide → 8-Bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

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Reaction Steps

A solution of N-trifluoroacetyl-8-bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (21 mg, 0.055 mmol) in methanol (2 mL) was treated with 15% aqueous NaOH (2 mL), and stirred overnight at 20 C. The product mixture was diluted with water (5 mL), extracted twice with EtOAc (10 mL), the combined organic phases were washed with brine (10 mL), dried with Na2SO4 and concentrated to give 11 mg of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.29 (s, 1 H), 6.64 (s, 1 H), 3.88 (s, 3 H), 3.02 (m, 2 H), 2.89 (dd, J=9, 14 Hz, 1 H), 2.80 (m, 1 H), 2.67 (d, J=14 Hz, 1 H), 2.53 (dd, J=10, 13, 1 H) 1.30 (d, J=7 Hz, 3 H), 1.19 (d, J=6 Hz, 3 H). MS calculated for C13H15BrNO+H: 284, observed: 284.

Provenance & Evidence