Sodium Hydroxide → HCID 18918218, compound

Participants

Reaction Steps

To a solution of the product of step (vi) (815 mg) in dry dichloromethane (10 ml) under argon was added a 1M solution of boron tribromide in dichloromethane (10 ml). The reaction was stirred at room temperature for 14 days, extra aliquots of BBr3 solution being added after 3 and 7 days. After 2 weeks, excess 1M aqueous sodium hydroxide solution was added, dropwise at first, and the mixture stirred at room temperature for 3 hours. The precipitated material was filtered off and the aqueous layer of the filtrate separated. The pH of the aqueous layer was adjusted to 8 by addition of 2N HCl (aq.) and 1M NaHClO3 (aq.) before being extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated to dryness to yield 1-benzyl-3-(4-(4-pyridyl)piperazin-1-yl)-4-quinolon-7-ol (75 mg) as an off-white solid: m.p. 141°-6° C.; NMR (d6DMSO) δ 3.10 (4H, m), 3.50 (4H, m), 5.40 (2H, s), 6.67 (1H, d), 6.72 (1H, dd), 6.90 (2H, m), 7.30 (5H, m), 7.76 (1H, s), 8.07 (1H, d), 8.15 (2H, s), 10.15 (1H, br, s); m/Z 413 (H+H)+.

Provenance & Evidence