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

HRID 985993Notes

Reaction equation

HRID 985993 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

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 99910956-(3-pyridyl)-2-(1H)-quinolone

Product 1

HCID 137288561-methyl-6-(3-pyridyl)-2-(1H)-quinolone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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).

Workup

  1. concentrationThe mixture was concentrated in vacuo, water (5 cm3)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate (3×10 cm3)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customthe residue chromatographed on silica (Merck "MK 60.9385")
  7. washeluting with chloroform
  8. customto yield a solid which
  9. customwas triturated with ether

Sources & evidence

ORD record
ord-d4eecf49b6734a2485ef314a7c5a0ccb
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

Loading…