Methanol → HCID 21949959, compound

Participants

Reaction Steps

To a solution of 5-methyl-1H-indole (1.00 g, 7.6 mmol) in diethyl ether (10 mL) at 4° C. was added a 2.0 M solution of oxalyl chloride in methylene chloride (4.0 mL, 8.0 mmol). The resulting solution was allowed to warm to room temperature and stirred for 1.5 h. The solution was cooled to −78° C. To this solution was added 25% (w/w) solution of sodium methoxide in methanol (3.65 mL, 16.0 mmol). The resulting solution was allowed to warm to room temperature. After one hour, the solution was filtered to give the title compound (1.16 g, 70%) as a light brown solid. 1H NMR (DMSO-d6) δ 8.31 (m, 1H), 7.95 (s, 1H), 7.42 (m, 1H), 7.11 (m, 1H), 3.88 (s, 3H), 2.41 (s, 3H).

Provenance & Evidence