Sodium Hydroxide → 1,2-Dihydro-6-(trifluoromethoxy)-2-(trifluoromethyl)-3-quinolinecarboxylic acid

HRID 650165Notes

Reaction equation

HRID 650165 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]([C:14]([F:17])([F:16])[F:15])[C:8]([C:18]([O:20]CC)=[O:19])=[CH:7]2.[OH-].[Na+]>CO.O>[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]([C:14]([F:15])([F:16])[F:17])[C:8]([C:18]([OH:20])=[O:19])=[CH:7]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21883532Ethyl 1,2-dihydro-6-(trifluoromethoxy)-2-(trifluoromethyl)-3-quinolinecarboxylate

Product 1

HCID 218836841,2-Dihydro-6-(trifluoromethoxy)-2-(trifluoromethyl)-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The ethyl 1,2-dihydro-6-(trifluoromethoxy)-2(trifluoromethyl)-3-quinolinecarboxylate from Step 4 (880 mg, 2.5 mmol) and 2.5 N aqueous sodium hydroxide (2 mL) were mixed in methanol (15 mL) and water (15 mL). The solution was heated on a steam bath for 2 hours. The reaction was allowed to cool to room temperature and was extracted with diethyl ether (50 mL). The aqueous layer was acidified (pH=1) with 3 N HCl and extracted with ethyl acetate (2×50 mL).

Workup

  1. temperatureThe solution was heated on a steam bath for 2 hours
  2. extractionwas extracted with diethyl ether (50 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)

Sources & evidence

ORD record
ord-244649276b284d29baeedc77eec37bfd
Source dataset
uspto-grants-2001_08
Patent number
US06271253B1

Reaction notes

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