Water → HCID 25160543, compound

HRID 1047748Notes

Reaction equation

HRID 1047748 reaction equation
C([O:3][C:4]([C:6]1([NH:19][C:20](=[O:32])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=2[O:28][CH:29]([CH3:31])[CH3:30])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH:29]([O:28][C:22]1[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]([NH:19][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=2)[CH2:7]1)=[O:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314379HCID 59314379, compound

Product 1

HCID 25160543HCID 25160543, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(2-isopropoxy-3-methyl-benzoylamino)-5-trifluoromethyl-indan-2-carboxylic acid ethyl ester (94) (690 mg, 1.5 mmol) and KOH (1.5 g, 18 mmol) is dissolved in EtOH (8 mL) and water (1 mL) under a water bath. The water bath is removed when KOH is completely dissolved. The resulting reaction solution is stirred at RT for 8 h. After concentration in vacuo, the residue is dissolved in water (30 mL) and acidified with conc. HCl until pH˜4. The precipitate is filtered to give a pure product (95) as a pale brown solid (495 mg, 78%).

Workup

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customThe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (30 mL)
  6. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-1f758d7568754f53930c989b9a06f891
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…