Sodium Hydroxide → 6-hydroxy-1-ethyl-1H-indole-3-carbonitrile

Participants

Reaction Steps

To a solution of 1-ethyl-6-methoxy-1H-indole-3-carbonitrile (2.85 g, 14.2 mmol), prepared by example 1A, step B, in CH2Cl2 (40 mL) was added a 1M solution of BBr3 in CH2Cl2 (28.5 mL, 28.5 mmol) at 0° C. The mixture was allowed to warm to room temperature and kept for 2.5 h. The dark reaction mixture was then poured onto ice and sufficient 1M NaOH was added until the pH was 8-9. The product was extracted with CH2Cl2 (3×) and the combined organic phases were washed with saturated NaHCO3 , H2O and saturated NaCl. After drying over MgSO4, the solution was concentrated and the product was purified by chromatography (EtOAc/CH2Cl2, 0-10%) to afford 2.15 g (82%) of 6-hydoxy-1-ethyl-1H-indole-3-carbonitrile as a yellow solid.

Provenance & Evidence