Hydrochloric Acid → Mefloquine carboxylic acid

HRID 2286278Notes

Reaction equation

HRID 2286278 reaction equation
[OH-:1].[Na+].[F:3][C:4]([F:17])([F:16])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11](=[O:14])[C:10]2=O.[F:18][C:19]([F:24])([F:23])[C:20]([CH3:22])=O.Cl>O>[F:18][C:19]([F:24])([F:23])[C:20]1[CH:22]=[C:10]([C:11]([OH:1])=[O:14])[C:9]2[C:13](=[C:5]([C:4]([F:17])([F:16])[F:3])[CH:6]=[CH:7][CH:8]=2)[N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9871Methyl trifluoromethyl ketoneHCID 14798Sodium HydroxideHCID 6045757-Trifluoromethylisatin2×

Product 1

HCID 169721Mefloquine carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100 parts by volume of water, 9.6 parts of sodium hydroxide, 43 parts of 7-trifluoromethylisatin and 26.8 parts of 1,1,1-trifluoroacetone is boiled for 6 hours, under atmospheric pressure, in a reaction vessel equipped with a stirrer, condenser, internal thermometer and feed device. The thin layer chromatogram of a sample taken after this reaction time and worked up with acid no longer shows any 7-trifluoromethyl-isatin. The batch is then allowed to cool, and 2 N hydrochloric acid is added, whilst stirring, until the pH is 2.5. The product which precipitates is washed with water and dried. 57 parts of 2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid, ie. 92.2% of theory, are obtained.

Workup

  1. customequipped with a stirrer, condenser
  2. temperatureto cool
  3. customThe product which precipitates
  4. washis washed with water
  5. customdried
  6. custom92.2% of theory, are obtained

Sources & evidence

ORD record
ord-b62fb85f175440c7972871e2edb5a2f6
Source dataset
uspto-grants-1982_04
Patent number
US04327215

Reaction notes

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