Chlorodifluoromethane → Methyl 8-difluoromethoxy-5-quinolinecarboxylate

HRID 1795751Notes

Reaction equation

HRID 1795751 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:23]([F:25])[F:24]>CN(C)C=O>[F:24][CH:23]([F:25])[O:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 22179176Methyl 8-hydroxyquinoline-5-carboxylate

Product 1

HCID 22179187Methyl 8-difluoromethoxy-5-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g (5.0 mmol) of methyl 8-hydroxy-5-quinolinecarboxylate was dissolved in 20 ml of dimethylformamide, 0.76 g (5.5 mmol) of potassium carbonate was added and 14 g of chlorodifluoromethane were introduced at 40° C. over a period of 2 hours. Solid components were then filtered off, the solvent was removed and the residue was washed with water and dried. This gave 0.75 g of a brown powder;

Workup

  1. filtrationSolid components were then filtered off
  2. customthe solvent was removed
  3. washthe residue was washed with water
  4. customdried

Sources & evidence

ORD record
ord-358e2192b0f24ae48f37affa86e14e5d
Source dataset
uspto-grants-2006_04
Patent number
US07030063B1

Reaction notes

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