Sodium Hydroxide → 1-Benzyl-4-hydroxy-6-methylquinolin-2(1H)-one

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Reaction Steps

The product from Step (3) was dissolved in 2N sodium hydroxide (150 ml) and the solution was refluxed for 4 hrs. Then the solution was cooled and acidified with mineral acid to pH3. The solid was filtered, dried and crystallized from ethyl acetate/hexane to give 1-benzyl-4-hydroxy-6-methyl-2(1H)-quinolinone (4.0 gm). That the expected product was obtained was confirmed by the spectral data: MS: m/e 265 (M·+); NMR (DMSO): δ 2.32 (s, 3H, CH3 --Ar), 5.43(s, 2H, CH2 --Ar), 5.96(s, 1H, =CH--), 11.48(s, 1H, OH) ppm.

Provenance & Evidence