Methyl iodide → HCID 20067132, compound

HRID 358887Notes

Reaction equation

HRID 358887 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]2[OH:20].[C:21](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[N:8]([CH3:21])[CH:7]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2=[O:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469677HCID 178469677, compound

Product 1

HCID 20067132HCID 20067132, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.60 g (0.0057 mole) of ethyl 6,7-difluoro-4-hydroxy-8-methoxyquinoline-3-carboxylate (IX) [prepared as described in step (B3) above] were dissolved in 20 ml of dimethylformamide, and 1.20 g (0.0085 mole) of potassium carbonate and 2.40 g (0.017 mole) of methyl iodide were added to the resulting solution. The mixture was then stirred at 60°-65° C. for 17 hours. At the end of this time, the solvent was distilled off under reduced pressure. The residue was extracted with methylene chloride, and the methylene chloride extract was washed with water, dried and concentrated by evaporation under reduced pressure to give 1.60 g of ethyl 6,7-difluoro-8-methoxy-1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (X, R9' =methyl) as a pale brown powder.

Workup

  1. distillationAt the end of this time, the solvent was distilled off under reduced pressure
  2. extractionThe residue was extracted with methylene chloride
  3. extractionthe methylene chloride extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-9b27eadf4f1246399ecd1b10fca1363d
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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