8-methoxy-2,3-dihydro-1H-3-benzazepin-2-one → 8-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

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Reaction Steps

To a solution of 8-methoxy-1,3-dihydro-benzo[d]azepin-2-one (10.33 g, 0.055 mol) in acetic acid (200 mL) was added palladium 10% wt on Carbon (50% wet; 2 g). The mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (50 PSI) overnight. Filtration through Celite and evaporation of solvent provided the crude product, which was triturated with a mixture of ether and DCM, filtered, and dried overnight in high vacuum to afford 8-methoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one. 1H-NMR (CDCl3) δ 7.03 (d, J=8.3 Hz, 1H), 6.76 (d, J=8.3 Hz, 1H), 6.69 (s, 1H), 6.17 (br s, 1H), 3.81 (s, 2H), 3.79 (s, 3H), 3.55 (q, J=5.1 Hz, 2H), 3.06 (t, J=5.8 Hz, 2H); LC/MS (ESI+): 192.07 (M+H).

Provenance & Evidence