Sodium hydride → 4-Benzyl-1-(1-pyridin-2-yl-2-quinolin-4-yl-ethylideneamino)-pyrrolidin-2-one

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Reaction Steps

A mixture of 3-benzyl-4-bromo-butyric acid(1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazide (PREP. 70, 0.8 g, 1.6 mmol) in tetrahydrofuran (26 mL) at 0° C. is treated with NaH (60% in mineral oil, 0.086 g, 2.2 mmol). The mixture is warmed to room temperature and stirred for 2 h. Saturated ammonium chloride (2 mL) is added and volatiles removed in vacuo. The residue is chromatographed on SiO2 (90% ethyl acetate/hexanes followed by dichloromethane:methanol:ammonium hydroxide/94:5:1) to yield the title compound, 0.4 g (45%), as a yellowish foam.

Provenance & Evidence