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

HRID 1047766Notes

Reaction equation

HRID 1047766 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 593142872-[3-Methyl-2-((Z)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 251594822-[3-Methyl-2-((Z)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acidYield 64.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-[3-methyl-2-((Z)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (124) (69 mg, 0.18 mmol) and KOH (500 mg, 8.9 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 5 h. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with conc. HCl until pH˜4. The precipitate is filtered to give a pure product (125) as white solid (42 mg, 64%).

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-9c77109066ff4b00a4cea91c97f5010d
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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