Water → HCID 20077451, compound

HRID 1655022Notes

Reaction equation

HRID 1655022 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:22]I.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8][C:9](=[O:13])[N:10]2[CH3:22])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 7227187-methoxy-4-phenyl-quinolin-2-ol

Product 1

HCID 20077451HCID 20077451, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 7-methoxy-4-phenyl-2-quinolinone from Example 1, Step 2 (1.62 g) in DMF (30 mL) was treated with NaH (60% in mineral oil; 310 mg). After stirring at 50° C. for 45 min., the mixture was cooled to r.t. and methyl iodide (0.6 mL) was added. After 30 min., H2O (100 mL) was added and the resulting solution extracted with EtOAc (3×). The organics were washed with H2O (2×), brine, dried (MgSO4) and the solvents evaporated. Flash chromatography of the residue (silica gel; CHCl3 /EtOAc (4:1)) provided the title compound as a foam.

Workup

  1. temperaturethe mixture was cooled to r.t.
  2. waitAfter 30 min.
  3. extractionthe resulting solution extracted with EtOAc (3×)
  4. washThe organics were washed with H2O (2×), brine
  5. dry with materialdried (MgSO4)
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-c8004835cb9f40c5a304476917eda2f1
Source dataset
uspto-grants-1995_04
Patent number
US05410054

Reaction notes

Loading…