Dimethylformamide → 6-Methoxy-1,3,3-trimethylindolin-2-one

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Reaction Steps

To a stirred ice cold suspension of sodium hydride (60% in mineral oil, 3.9 g, 98.1 mmol) in 50 mL of dry DMF was added solid 6-methoxy-1,3-dihydro-indol-2-one (4.00 g, 24.5 mmol) portionwise over 10 minutes. To the resultant gray mixture was added dropwise MeI (2.68 g, 98.1 mmol). The mixture was warmed to room temperature and stirred for 45 minutes, and then was cooled back to 0° C. and quenched with 90 mL of water. The mixture was extracted with an ethyl acetate (EtOAc)/toluene mixture (2:1), and the extracts were dried with magnesium sulfate (MgSO4), treated with activated charcoal, filtered and concentrated to give a red syrup. Silica gel chromatography (1:10 EtOAc/hexanes) gave 4.16 g (83%) of the title compound as a white solid (mp 67–69° C.). Mass spectrum m/e calcd for M+H=234.1. Found 234.2.

Provenance & Evidence