Indole → Indole-3-Carboxaldehyde

Participants

Reaction Steps

1H-Indole (10 g, 85.360 mmol) in DMF (10 mL) was added dropwise to a stirred solution of POCl3 (8.67 mL, 93.896 mmol) in DMF over a period of 10 minutes at 0° C. The resulting mixture was stirred at room temperature for 1 hour. The reaction was monitored by TLC (40% ethylacetate in hexane). The reaction mixture was quenched with chilled water, followed by the addition of aqueous NaOH solution and refluxed at 100° C. for 15 minutes. The reaction mixture was cooled to room temperature and maintained at 0° C. overnight. The precipitate formed was collected, washed with water and dried to afford 11.6 g of the product (94% yield).

Provenance & Evidence