Acetonitrile → 6-Chloro-5-(4-methoxy-phenyl)-1H-indole-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

6-Chloro-5-(4-methoxy-phenyl)-1H-indole (25.0 g, 97 mmol), (chloromethylene)dimethyliminium chloride (18.8 g, 147 mmol) and MeCN (100 mL) were stirred at room temperature for 20 minutes. To the resulting bright yellow slurry was added 1 N NaOH (400 mL, 400 mmol) and water (400 mL). The reaction mixture was heated to 100° C. for 45 minutes, then cooled to 0° C. The slurry was filtered, and the collected solid was washed with water and air dried to afford the title compound as a yellow solid. MS (ES+) 286.5 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 10.06 (s, 1 H), 8.74 (br. s., 1 H), 8.29 (s, 1 H), 7.87 (d, J=2.93 Hz, 1 H), 7.58 (s, 1 H), 7.42 (d, J=8.54 Hz, 2 H), 6.98 (d, J=8.54 Hz, 2 H), 3.88 (s, 3 H)

Provenance & Evidence