Water → 2-[2-(-1-Ethyl-but-1-enyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid

HRID 1047770Notes

Reaction equation

HRID 1047770 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:30])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[C:24]([CH2:28][CH3:29])=[CH:25][CH2:26][CH3:27])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH2:28]([C:24]([C:18]1[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:30])=[CH:25][CH2:26][CH3:27])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 685911652-[2-(-1-Ethyl-but-1-enyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 685896612-[2-(-1-Ethyl-but-1-enyl)-3-methyl-benzoylamino]-indan-2-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-[2-(-1-ethyl-but-1-enyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid ethyl ester (128) (503 mg, 1.24 mmol) and KOH (1 g, 17.9 mmol) is dissolved in EtOH (10 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 (40 mL) and acidified with conc. HCl until pH˜3. The precipitate is filtered to give a pure product (129) as a brown solid (452 mg, 97%).

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 (40 mL)
  6. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-4c31ee0f98a04c42a289fcc6515e5b29
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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