Water → 2-[3-Methyl-2-((E)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid

HRID 1047786Notes

Reaction equation

HRID 1047786 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][CH2:27][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>[CH3:23][C:19]1[C:18](/[CH:24]=[CH:25]/[CH2:26][CH2:27][CH3:28])=[C:17]([CH:22]=[CH:21][CH:20]=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:29]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593142302-[3-Methyl-2-((E)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 251594852-[3-Methyl-2-((E)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acidYield 102.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture 2-[3-methyl-2-((E)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (145) (170 mg, 0.43 mmol) and KOH (60 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 (146) as white solid (160 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-a074f5bc5d4a4794a3217f88b29b84a7
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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