Lithium Hydroxide → HCID 9886988, compound

Participants

Reaction Steps

To a solution of ethyl 4-(2-(4,4-dimethyl-1,2,3,4-tetrahydro-N-(4-methylphenyl)quinolin-7-yl)ethynyl)benzoate (Compound 4) (0.105 g, 0.25 mmol) in 10.0 mL of tetrahydrofuran and 0.5 mL of methanol was added 1.0 mL (1.5 mmol) of 1.5M aqueous LiOH. The resulting solution was stirred at room temperature for 24 hours. The mixture was concentrated in vacuo, water was added, and the mixture was extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give the title compound as a yellow solid, which was recrystallized from 2:1 acetonitrile:ethyl acetate to give yellow needles. PNMR (300 MHz, DMSO) d 1.31 (6 H, s), 1.80 (2 H, t, J=5.9 Hz), 2.31 (3 H, s), 3.53 (2 H, t, J=5.9 Hz), 6.50 (1 H, d, J=1.6 Hz), 6.83 (1 H, dd, J=8.0, 1.6 Hz), 7.16 (2 H, d, J=8.4 Hz), 7.25 (2 H, J=8.4 Hz), 7.29 (1 H, d, J=8.0 Hz), 7.55 (2 H, d, J=8.4 Hz), 7.89 (2 H, d, J=8.4 Hz)

Provenance & Evidence