Dimethyl Sulfate → 1-methyl-6-(3-pyridyl)-2-(1H)-quinolone

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]3)[CH:2]=1.[H-].[Na+].S(OC)(O[CH3:24])(=O)=O>CN(C=O)C>[CH3:24][N:13]1[C:14]2[C:9](=[CH:8][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:16][CH:15]=2)[CH:10]=[CH:11][C:12]1=[O:17]

Participants

Procedure

A stirred solution of 6-(3-pyridyl)-2-[1H]-quinolone (0.05 g) in DMF (0.5 cm3) was treated at room temperature with sodium hydride (0.012 g of a 50% dispersion in oil) for 1 hour. A solution of dimethyl sulphate (0.016 g) in DMF (0.2 cm3) was added and the mixture was stirred for 1.5 hours. The mixture was concentrated in vacuo, water (5 cm3) was added and the mixture was extracted with ethyl acetate (3×10 cm3). The combined organic extracts were dried (MgSO4), concentrated in vacuo and the residue chromatographed on silica (Merck "MK 60.9385") eluting with chloroform to yield a solid which was triturated with ether to afford 1-methyl-6-(3-pyridyl)-2-(1H)-quinolone 0.25H2O, m.p. 116°-118°, (0.02 g).