Methanol → HCID 9967433, compound

Participants

Reaction Steps

The mixture of [1-methyl-5-(4-trifluoromethyl-phenyl)-1H-indol-3-yl]-acetonitrile (0.230 g, 0.732 mmol), potassium hydroxide (2.16 g, 38.5 mmol), methanol (5 mL) and water (5 mL) was heated at refluxed for 24 hours. The reaction mixture was cooled to room temperature and concentrated. Water was added and the mixture was acidified with 2N hydrochloric acid. The mixture was extracted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to dryness. Purification of the residue by HPLC using 4% methanol in methylene chloride as the mobile phase afforded the title compound as a light brown solid (0.0598 g, 25%), mp 167-168° C. Mass spectrum (+APCI, [M+H]+) m/z 334. 1HNMR (400 MHz, DMSO-d6): δ 12.1-12.4 (br s, 1H), 7.9 (d, 3H, J=7.8 Hz), 7.8 (d, 2H, J=8.1 Hz), 7.55 (d, 2H, J=1.2 Hz), 7.3 (s, 1H), 3.8 (s, 3H) and 3.7 ppm (s, 2H). Elemental Analysis for C18H14F3NO2: Calculated: C, 64.86; H, 4.23; N, 4.20. Found: C, 64.88; H, 4.17; N, 4.03.

Provenance & Evidence