Water → HCID 20063333, compound

Participants

Reaction Steps

A stirred solution of crude 2-(4-fluorophenyl)-4-isopropyl-1-oxo-1,2-dihydroisoquinoline-3-carbonyl chloride (21 g) in dry tetrahydrofuran (300 ml) was treated dropwise with a solution of lithium borohydride in tetrahydrofuran (26 ml; 2.0M) and the mixture stirred at room temperature for 18 hours. The reaction mixture was then treated dropwise with water (50 ml), diethyl ether (500 ml) and more water (200 ml) and the organic layer was separated, washed with water (200 ml) and brine (200 ml), dried over magnesium sulphate and evaporated to leave a yellow oil. This was triturated with a hot mixture of diethyl ether (200 ml) and n-hexane (400 ml) to give 2-(4-fluorophenyl)-3-hydroxymethyl-4-isopropyl-1-oxo-1,2-dihydroisoquinoline (13.7 g) in the form of a white solid, m.p. 157°-158° C. [Elemental analysis: C, 73.1; H, 5.7; N, 4.4%; calculated: C, 73.3; H, 5.8; N, 4.5%; NMR (in CDCl3): 1.55 (7H, d, J=8 Hz,), 3.65 (1H, sept, J=8 Hz), 4.4 (2H, s), 7.1-7.4 (4H, m), 7.5 (1H, t, J=8 Hz,), 7.7 (1H, t, J=8 Hz), 8.04 (1H, d, J=8 Hz), 8.5 (1H, d, J=8 Hz)].

Provenance & Evidence