Water → 2-[2-(3-Methoxy-propenyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid

HRID 1047842Notes

Reaction equation

HRID 1047842 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][CH2:26][O:27][CH3:28])[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>[CH3:28][O:27][CH2:26][CH:25]=[CH: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])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:29]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 685889372-[2-(3-Methoxy-propenyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 685908492-[2-(3-Methoxy-propenyl)-3-methyl-benzoylamino]-indan-2-carboxylic acidYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product (220) and KOH (1.0 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 3 h. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with conc. HCl until no more white precipitate formed. After the filtration, the obtained brown solid is purified by HPLC to give pure product (221) as white solid (200 mg, 62%).

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. customformed
  7. filtrationAfter the filtration
  8. customthe obtained brown solid is purified by HPLC

Sources & evidence

ORD record
ord-305ba7a9d3ab4728b3141084e1934352
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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