Dimethylformamide → 3-Formyl-1H-indole-5-carbonitrile

Participants

Reaction Steps

Add phosphorous oxychloride (11.76 g, 76.67 mmol) dropwise to DMF (24.3 ml) wile maintaining the temperature at less than 10° C. Warm to ambient temperature and stir for 15 minutes at ambient temperature. Add dropwise 5-cyanoindole (10.00 g, 70.34 mmol) as a solution in DMF (30 ml) while keeping the temperature below 35°. After 1 hour, pour the reaction mixture into ice/water (300 ml) and then add 5N NaOH (54 ml) with stirring Add slowly an additional amount of 5N NaOH (19.7 ml) and then heated to 90° for 1 minute and then cooled to ambient temperature to give a precipitate. Filter the precipitate and washed with water and dry to give the title compound: mp 248-250° C. MS (ACPI): m/e 171.0 (M+1). Analysis for C10H6N2O: Calcd: C, 70.58; H, 3.55; N, 16.46. found: C, 70.41; H, 3.53; N, 16.33.

Provenance & Evidence