Water → HCID 14810857, compound

Participants

Reaction Steps

Methyl iodide (30 g) was added to a stirred mixture of 7-methylindole-3-carboxylic acid (4.3 g) and powdered potassium hydroxide (20 g) in anhydrous acetone at 0° C. The resulting suspension was then stirred at room temperature overnight, then poured into water (500 ml), washed with dichloromethane (3×100 ml) and the aqueous phase acidified to pH 2 with hydrochloric acid. The product was isolated by filtration and dried under vacuum to afford white crystals (4.5 g); m.p. 243° C.; δH (360 MHz, DMSO-d6) 2.72 (3H, s, CH3), 4.09 (3H, s, NCH3), 6.92 (1H, d, J=6 Hz, H-6), 7.02 (1H, t, J=6 Hz, H-5), 7.87 (1H, d, J=6, H-4), 7.92 (1H, s, H-2); m/z 189 (M+, 100%), 172 (40), 144 (30), 91 (55).

Provenance & Evidence