Ammonium Hydroxide → HCID 67980295, compound

Participants

Reaction Steps

To a solution of 6-benzyloxyindole-acetic acid (4.72 g, 16.7 mmol) in tetrahydrofuran (100 mL), was added carbonyl diimidazole (2.85 g, 17.6 mmol). The resulting solution was stirred at room temperature for 1.5 hr. Ammonium hydroxide (14 mL) was added and the reaction was allowed to stir at room temperature for 18 h. The mixture was concentrated to ½ volume and the resulting solid filtered and washed with cold methanol to give 2-[6-(benzyloxy)-1H-indol-3-yl]acetamide (4.7 g, quantitative) as a off-white solid. Mp: 189-192° C.; 1H NMR (DMSO-d6) 400 MHz δ: 10.65 (brs, 1H), 7.46 (d, J=7.4 Hz, 2H), 7.37-7.35 (m, 2H), 7.31 (m, 1H), 7.26 (brs, 1H), 7.14 (d, J=2.3 Hz, 1H), 7.12 (d, J=2.3 Hz, 1H), 6.79 (m, 2H), 5.04 (s, 2H), 3.39 (s, 2H); LCMS [M+H]: 281.

Provenance & Evidence