Hydrochloric Acid → HCID 24957323, compound

Participants

Reaction Steps

To a solution of 4-imidazol-1-yl-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one (80 mg, 0.332 mmol) in THF (3 mL) at room temperature is added BH3-THF (3.3 mL, 1.0 M solution) and the mixture is stirred at room temperature for 1 h. To the reaction mixture is added 6N HCl until no hydrogen gas evolves from the solution. The reaction mixture is stirred for 2 h at room temperature and is added aqueous 10% NaOH to adjust PH=12 and then the mixture is extracted into CH2Cl2 and washed by brine; dried with anhydrous sodium sulfate and concentrated to give the crude compound. Reverse phase HPLC (CH3CN:H2O=20 to 90% over 20 mins) purification gives the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.85 (s, 3 H), 1.06 (s, 3 H), 2.92-3.00 (m, 1 H), 3.12 (d, J=11.9 Hz, 1 H), 4.18 (br. s., 1 H), 4.78 (s, 1 H), 6.57-6.66 (m, 2 H), 6.80 (s, 1 H), 6.86 (d, J=7.1 Hz, 1 H), 7.02 (s, 1 H), 7.07-7.14 (m, 1 H), 7.47 (s, 1 H).

Provenance & Evidence