HCID 68917915, compound → HCID 68915072, compound

Participants

Reaction Steps

To a solution of 5-methoxy-1-(4′-methoxybenzoyl)-1H-indole-2-carboxylic acid (7.02 g, 21.57 mmol) in ethanol (200 mL) was added platinum oxide (0.7 g). The mixture was hydrogenated for 6 hours at 32 psi. The reaction mixture was filtered through a pad of Celite. The filter cake was washed with ethanol. The combined filtrate and washings was evaporated in vacuo to dryness. The solid residue was recrystallized from ethanol to yield 5-methoxy-1-(4′-methoxybenzoyl)-2,3-dihydro-1H-indole-2-carboxylic acid, 6.35 g (90%): mp 151-152° C.; 1H NMR (DMSO-d6) δ 3.05 (1H, m, CH), 3.56-3.63 (1H, m, N—CH), 3.70 (3H, s, OMe), 3.81 (3H, s, OMe), 4.97-5.01 (1H, m, CH), 6.67 (1H, br, ArH), 6.86 (2H, m, 2×ArH), 7.00 (2H, d, J=8.6 Hz, 2×H), 7.45 (2H, J=8.6 Hz, 2×ArH), 12.92 (1H, brs, exchangeable, OH). Anal. Calcd. for C18H17NO5.0.1H2O: C, 65.69; H, 5.26; N, 4.25. Found: C, 65.61; H, 5.48; N, 4.17.

Provenance & Evidence