Methanol → 5-Bromo-1-(4-hydroxyphenyl)-2-methyl-1H-indole-3-carbaldehyde oxime

Participants

Reaction Steps

A mixture of 5-bromo-1-(4-hydroxyphenyl)-2-methyl-1H-indole-3-carbaldehyde (0.16 g, 0.5 mmol), hydroxylamine hydrochloride (0.10 g, 1.4 mmol), methanol (10 mL) and pyridine (0.2 mL) was reacted according to the procedure used in Example 4 to afford a white solid (66%): mp 209-211° C.; 1H NMR (DMSO-d6): δ 2.29 (3H, s), 6.92-6.97 (3H, m), 7.20-7.25 (3H, m), 8.19 (1 H, d, J=1.9 Hz), 8.39 (1H, s), 9.94 (1H, br s), 10.76 (1H, s); MS m/z (M+H)+ 345/347 (1 Br). Anal. for C16H13BrN2O2·0.5H2O; Calc'd: C, 54.26; H, 3.98 N, 7.91. Found: C, 54.26; H, 3.68; N, 7.65.

Provenance & Evidence