Potassium Hydroxide → HCID 10236477, compound

Participants

Reaction Steps

To a deoxygenated solution of 3-(2-acetylthioethyl)-1-phenyl-1H-indole-2-carboxylic acid, methyl ester in dioxane (5 mL) was added a deoxygenated solution of potassium hydroxide (0.168 g, 3.0 mmol) in water (5 mL). The reaction mixture was stirred overnight. Volatile solvent was removed under reduced pressure and the remaining mixture was poured into 1 N HCl (25 mL) containing ice chips. The resulting white precipitate was washed with H2O and dried under vacuum to give 0.110 g of 3-(2-mercaptoethyl)-1-phenyl-1H-indole-2-carboxylic acid (93% yield) as a white solid: 1H NMR (CDCl3) δ 1.52 (t, J=8.1 Hz, 1H), 2.91 (q, J=7.7 Hz, 2H), 3.49 (t, J=7.6 Hz, 2H), 7.08 (d, J=8.2 Hz, 1H), 7.21 (t, J=7.5 Hz, 1H), 7.27–7.33 (m, 3H), 7.42–7.53 (m, 3H), 7.78 (d, J=8.0 Hz, 1H). Anal. Calcd. for C17H15N2O2S.0.25 H2O: C, 67.64, H, 5.18, N, 4.64, S, 10.62. Found: C, 67.77, H, 5.15, N, 4.69, S, 10.62.

Provenance & Evidence