Water → 4-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]benzoic acid

HRID 230616Notes

Reaction equation

HRID 230616 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)[N:4]=1.[OH-].[Na+].O>C(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 4861010HCID 4861010, compound

Product 1

HCID 8918604-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]benzoic acidYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]benzoate (600 mg, 1.85 mmol), sodium hydroxide (81 mg, 2.0 mmol), in ethanol (4 ml) and water (4 ml) was stirred at reflux for 1 hour. The reaction mix was allowed to cool and the ethanol was removed under reduced pressure and the residue was partitioned between diethyl ether (10 ml) and water (10 ml). The aqueous layer was separated and made acidic with 2N HCl, then extracted with dichloromethane. The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a beige solid (222 mg, 39%)

Workup

  1. temperatureat reflux for 1 hour
  2. additionThe reaction mix
  3. temperatureto cool
  4. customthe ethanol was removed under reduced pressure
  5. customthe residue was partitioned between diethyl ether (10 ml) and water (10 ml)
  6. customThe aqueous layer was separated
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic layer was dried over sodium sulphate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-93c3104ba55b4abe89929ff48c9c6610
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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