Sodium borohydride → 1-hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone

Participants

Reaction Steps

A solution of 1-hexyl-3-formyl-4-methoxy-6-methyl-2(1H)-quinolinone (Step (2) of Example 1, 10 g) in methanol (80 ml) was cooled in an ice-bath and stirred while adding, in small lots, solid sodium borohydride (0.5 g). After stirring for an additional 5 mins the reaction mixture was carefully diluted with water and extracted with methylene chloride. The extracts are dried and evaporated under reduced pressure. The crude product is chromatographed on silica-gel. Elution with 30% acetone-hexane gave 1-hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone. That the expected product was obtained was confirmed by the spectral data: MS: m/e 303 (M+); NMR (CDCl3): δ4.0 (s, H, OCH3), 4.75 (d, 2H, CH2O).

Provenance & Evidence