Water → 2-[2-(-2-Cyclopropyl-vinyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid

HRID 1047779Notes

Reaction equation

HRID 1047779 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[CH:24]=[CH:25][CH:26]2[CH2:28][CH2:27]2)[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>[CH:26]1([CH:25]=[CH:24][C:18]2[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7]2)=[O:29])[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 685906612-[2-(-2-Cyclopropyl-vinyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 685904222-[2-(-2-Cyclopropyl-vinyl)-3-methyl-benzoylamino]-indan-2-carboxylic acidYield 103.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture 2-[2-(-2-cyclopropyl-vinyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid ethyl ester (137) (220 mg, 0.56 mmol) and KOH (600 mg, 10.7 mmol) is dissolved in EtOH (8 mL) and water (0.5 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 (20 mL) and acidified with conc. HCl until no more precipitate came out of the water. The precipitate is filtered to give a pure product (138) as white solid (209 mg, 100%).

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 (20 mL)
  6. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-24887ccad6b847d8bab092b77c96b4a8
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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