Water → {4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}acetic acid

HRID 230619Notes

Reaction equation

HRID 230619 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]CC)=[O:20])=[CH:14][CH:13]=2)[N:4]=1.[OH-].[Na+].O>C(O)C>[F:25][C:2]([F:1])([F:24])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=2)[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 57762789Ethyl {4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}acetate

Product 1

HCID 50992931{4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}acetic acidYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl {4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}acetate (0.92 g, 2.61 mmol), sodium hydroxide (114 mg, 2.85 mmol), in ethanol (10 ml) and water (10 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 made acidic with 5N HCl, then extracted into dichloromethane. The organic layer was added to a 5 g pre-packed column and eluted from 0-100% ethyl acetate in petroleum ether to give the title compound as a pale yellow solid (0.42 g, 50%).

Workup

  1. temperatureat reflux for 1 hour
  2. additionThe reaction mix
  3. temperatureto cool
  4. customthe ethanol was removed under reduced pressure
  5. extractionextracted into dichloromethane
  6. additionThe organic layer was added to a 5 g pre-packed column
  7. washeluted from 0-100% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-21d6b82d5ae34bf78611b56b869e6d1d
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

Loading…