Water → HCID 68281244, compound

Participants

Reaction Conditions

Reaction Steps

A reactor was charged with 1.5 g (10 mmol) of 3,4-dihydroquinolin-2(1H)-one and 77 mL of tetrahydrofuran as a solvent. After cooling the mixture to 0° C., 0.8 g (20 mmol) of sodium hydride was added dropwise to the mixture. The mixture was stirred for 30 minutes, and held at 0° C., followed by the addition of 5.12 g (30 mmol) of benzyl chloroformate (acyl chloride (RCl)) and 0.24 g (2 mmol) of N,N-dimethyl-4-aminopyridine (DMAP). After adjusting the temperature of the reaction system to room temperature (about 20° C.), the mixture was reacted for 12 hours with stirring. After cooling the mixture including the reaction product to 0° C., water was added dropwise to the mixture, followed by extraction with ethyl acetate. After the addition of excess anhydrous magnesium sulfate to the resulting organic layer, the solvent was evaporated under reduced pressure to obtain a concentrate including a crude product. The concentrate was subjected to silica gel flash column chromatography (eluant: hexane/ethyl acetate=1/1) to obtain benzyl 2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (yellow oily product) represented by the following formula (ai2) having a Cbz group (PhCH2OCO—) as a protecting group (yield: 76%). The analysis data for the resulting compound (ai2) is shown below.

Provenance & Evidence