Hydrochloric Acid → HCID 3595778, compound

Participants

Reaction Steps

Aqueous sodium hydroxide (4M, 75 mL) was added to ethyl 5-methyl-2-phenyl-1H-indole-3-acetate (Description 5, 1.61 g) in methanol (150 mL) and the mixture was stirred at room temperature for 2 h. The mixture was cooled to 0° C. , the pH was adjusted to 3.0 with hydrochloric acid (2M) and the mixture was extracted with ethyl acetate. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was recrystallized from ether to give the title compound as a colourless solid (1.1 g, 76%). 1H NMR (360 MHz, CDCl3) δ2.47 (3H, s), 3.85 (3H, s), 7.05 (1H, dd, J 8.3, 1.4 Hz), 7.27 (1H, d, J 11.2 Hz), 7.36-7.49 (4H, m), 7.62 (1H, d, J 9.2 Hz), and 8.05 (1H, br s). m/z (ES+) 266 (M+1).

Provenance & Evidence