Water → 2-(2-Isopropoxy-3-methyl-benzoylamino)-5,6-dimethyl-indan-2-carboxylic acid

HRID 1047745Notes

Reaction equation

HRID 1047745 reaction equation
C([O:3][C:4]([C:6]1([NH:17][C:18](=[O:30])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=2[O:26][CH:27]([CH3:29])[CH3:28])[CH2:14][C:13]2[C:8](=[CH:9][C:10]([CH3:16])=[C:11]([CH3:15])[CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH:27]([O:26][C:20]1[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]([NH:17][C:6]1([C:4]([OH:5])=[O:3])[CH2:7][C:8]2[C:13](=[CH:12][C:11]([CH3:15])=[C:10]([CH3:16])[CH:9]=2)[CH2:14]1)=[O:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593142212-(2-Isopropoxy-3-methyl-benzoylamino)-5,6-dimethyl-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593143372-(2-Isopropoxy-3-methyl-benzoylamino)-5,6-dimethyl-indan-2-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(2-isopropoxy-3-methyl-benzoylamino)-5,6-dimethyl-indan-2-carboxylic acid ethyl ester (90) (440 mg, 1.07 mmol) and KOH (1 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 and 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 no more precipitate formed. The precipitate is filtered to give the pure product (91) as a pale brown solid (374 mg, 92%).

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. customformed
  7. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-5607709de1bd40029b32128c5274d644
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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