Diethyl Ether → 3,4-Dimethoxy-1-methylquinolin-2(1H)-one

Participants

Reaction Steps

A suspension of 1-methyl-3,4-dihydroxy-2(1H)-quinolinone (0.2 gm, Example 7, obtained from Formula 1.02, see Example 1) in methylene chloride (5 ml) and methanol (5 ml) was treated with a solution of excess diazomethane in ether. The resulting solution was evaporated and the residue was chromatographed on silica gel (5 gm). The major product of the reaction was eluted with 1% methanol/methylene chloride and crystallized from ethyl acetate-hexane to give the title compound. That the expected product was obtained was confirmed by the spectral data: MS: m/e 219 (M.+ +1); NMR(CDCl3): δ3.71 (s, 3H, CH3 --N), 3.94 (s, 3H, OCH3), 4.22 (s, 3H, OCH3) ppm.

Provenance & Evidence