Ammonia → 4H-Imidazo[4,5,1-ij]quinolin-2(1H)-one,5,6-dihydro-5-(propylamino)-, (5R)-

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Reaction Steps

Sodium cyanoborohydride (0.17 g) was added in small portions over a 5-hour period to a stirred solution of 1.90 g (8.4 mmol) 5-amino-5,6-dihydro-4H-imidazo(4,5,1-ij)quinolin-2(1H)-one, 0.85 mL sodium methoxide and 1.5 g propionaldehyde in methanol (175 mL). Methanolic ammonia solution was added, and after 30 minutes, the solvent was evaporated. The residual oil was partitioned between ethyl acetate and water and the crude product obtained by evaporating the ethyl acetate was dissolved in chloroform and chromatographed on silica gel eluting with 2.5% methanol:chloroform to give 1.24 g (64% yield) of 5,6-dihydro-5-(propylamino)-4H-imidazo(4,5,1-ij)quinolin-2(1H)-one.

Provenance & Evidence