Diisopropylamine → HCID 9883205, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (0.2 mL, 1.43 mmol) in THF (3 mL) at 0° C. was added n-butyllithium (0.9 mL of a 1.6 M solution in hexane, 1.44 mmol). After stirring at 0° C. for 10 minutes, the resulting lithium diisopropylamide solution was treated with a solution of N-benzyl-2-methylbenzamide (145 mg, 0.64 mmol) in THF (2 mL). The resulting deep purple solution was stirred at 0° C. for 75 minutes at which time it was treated with a solution of N-methoxy-N-methyl-benzamide (117 mg, 0.71 mmol) in THF (2 mL). After slowly warming to ambient temperature over 100 minutes the reaction was quenched by the addition of 3N HCl (12 mL). The biphasic mixture was then heated to reflux with vigorous stirring. After 1 hour at reflux the reaction mixture was allowed to cool to ambient temperature. After cooling, the reaction was diluted with ether (50 mL), and basified by careful addition of solid Na2CO3. The basic aqueous was extracted with ether (3×20 mL), combined organics were washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under educed pressure to afford a pale orange oil. The crude product was purified by silica gel column chromatography eluting with a gradient from 0% to 20% ethyl acetate/hexane on a 20 g silica column. The product peak was collected to afford 2-benzyl-3-phenyl-2H-isoquinolin-1-one (22 mg, 11% yield) as a clear oil that slowly solidified to a white waxy solid. 1H-NMR (400 MHz, CDCl3): δ 8.49 (1H, d J=8.3 Hz), 7.68-7.63 (1H, m), 7.53-7.48 (2H, m), 7.42-7.37 (1H, m), 7.35-7.30 (2H, m), 7.22-7.14 (5H, m), 6.92-6.88 (2H, m), 6.45 (1H, s), 5.25 (2H, s) ppm.

Provenance & Evidence