Sodium Hydroxide → 8-Difluoromethoxy-5-quinolinecarboxylic acid

HRID 1795752Notes

Reaction equation

HRID 1795752 reaction equation
[F:1][CH:2]([F:18])[O:3][C:4]1[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]([C:14]([O:16]C)=[O:15])=[CH:6][CH:5]=1.[OH-].[Na+]>O>[F:18][CH:2]([F:1])[O:3][C:4]1[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]([C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22179187Methyl 8-difluoromethoxy-5-quinolinecarboxylate

Product 1

HCID 221791908-Difluoromethoxy-5-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

0.7 g (2.8 mmol) of methyl 8-difluoromethoxy-5-quinolinecarboxylate was suspended in 15 ml of water and 0.4 g (10 mmol) of sodium hydroxide was added. The mixture was stirred at 25° C. for 20 hours and then filtered off, and the filtrate was washed with methyl tert-butyl ether. The aqueous phase was adjusted to pH 3 using concentrated hydrochloric acid and filtered off, and the residue was dried. This gave 0.45 g of a colorless powder;

Workup

  1. filtrationfiltered off
  2. washthe filtrate was washed with methyl tert-butyl ether
  3. filtrationfiltered off
  4. customthe residue was dried

Sources & evidence

ORD record
ord-2a787d84f0d3443e8a2803bb158b2002
Source dataset
uspto-grants-2006_04
Patent number
US07030063B1

Reaction notes

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