Hydrochloric Acid → HCID 67081826, compound

Participants

Reaction Steps

To a solution of Step A. 2,2-dimethyl-3-oxo-2,3-dihydro-1H-indene-5-carbonitrile (17.8 g, 0.096 mol) in ethanol at 0° C. was added NaBH4 (7.27 g, 0.192 mol) as a solid and the resulting mixture was warmed to rt gradually and stirred for ˜16 h. After cooling to 0° C., aq HCl (1N, 300 mL) was added slowly with vigorously stirring. After additional stirring at 0° C. for 30 min and rt for 2 h, the reaction mixture was concentrated to remove ethanol, then extracted with EtOAc (400 mL). The aqueous portion was further extracted with EtOAc (100 mL×3). The combined organic extracts were washed with water (80 mL×2), sat. aq. NaHCO3 (80 mL), brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound as a colorless oil. HPLC Ret. time: 2.62 min. LCMS MH+ (m/z) 188.33. 1H NMR: (DMSO-d6, 400 MHz): δ 7.65 (s, 1H), 7.62 (d, 1H), 7.38 (d, 1H), 5.49 (d, 1H), 4.59 (d, 1H), 2.70 (m, 2H), 1.13 (s, 3H), 0.83 (s, 3H).

Provenance & Evidence