p-Anisoyl chloride → HCID 68917915, compound

Participants

Reaction Steps

To a solution of commercially available 5-methoxyindole-2-carboxylic acid (6.69 g, 35 mmol) and triethylamine (10 mL, 71.7 mmol) in anhydrous CH2Cl2 (70 mL) containing catalytic amount of DMAP was added dropwise a solution of 4-methoxybenzoyl chloride (6.20 g, 36.34 mmol) in CH2Cl2 (15 mL) at 0° C. The reaction mixture was stirred at this temperature for 15 min and then at room temperature for 4 hours. The reaction mixture was washed successively with 5% aqueous KHSO4 solution (2×20 mL), brine (25 mL), dried over Na2SO4, and evaporated under reduced pressure to dryness. The solid residue was recrystallized from methanol to yield 5-methoxy-1-(4′-methoxybenzoyl)-1H-indole-2-carboxylic acid as a white solid (7.4 g, 65%): mp 185-187° C.; 1H NMR (DMSO-d6) δ 3.80 and 3.85 (each 3H, s, 2×OMe), 7.02 (1H, dd, J=2.5 Hz and J=9.0 Hz, ArH), 7.07 (2H, d, J=8.9 Hz, 2×ArH), 7.28 (1H, d, J=2.5 Hz, ArH), 7.33 (1H, s, ArH), 7.38 (1H, d, J=9.0 Hz, ArH), 7.59 (2H, d, J=8.9 Hz, 2×ArH), 13.2 (1H, brs, exchangeable, OH). Anal. Calcd. for C18H15NO5.0.1H2O: C, 65.73; H, 4.65; N, 4.25. Found: C, 65.77; H, 4.61; N, 4.24.

Provenance & Evidence