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Hydrochloric Acid → 8-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 418175
Notes
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Reaction equation

HRID 418175 reaction equation
C([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]2=[N:8][CH:7]=1)=[O:5])C.O[Li].O.Cl.[Na+].[Cl-]>C1COCC1.CO.O>[F:18][C:15]([F:16])([F:17])[C:14]1[C:9]2[N:10]([C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=2)[CH:11]=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 866116258-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester

Product 1

HCID 866116268-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents

3
HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of the above 8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (3.06 g, 7.61 mmol) in THF (45 mL), MeOH (5 mL) and water (11.3 mL) at 23° C. was added LiOH.H2O (479 mg, 11.41 mmol) and the mixture was stirred at 23° C. for 3 h. Poured into ice water, adjusted pH with 1 N HCl (about 11.41 mL) to pH 2-3, saturated with solid NaCl, extracted with EtOAc, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a light brown solid (2.87 g, 101%). MS (ISN) 373 [(M−H)−]; mp 248° C. (dec.).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. customRemoval of the solvent in vacuum
  4. waitleft the title compound as a light brown solid (2.87 g, 101%)

Sources & evidence

ORD record
ord-cd9c8133a30640e181272a859ae5a8d9
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093263B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes