Water → 2-[3-methyl-2-(2-methylprop-1-en-1-yl)benzamido]-2,3-dihydro-1H-indene-2-carboxylic acid

HRID 1047776Notes

Reaction equation

HRID 1047776 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[CH:24]=[C:25]([CH3:27])[CH3:26])[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]=[C:25]([CH3:27])[CH3:26])=[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:28]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593140782-[3-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 251606722-[3-methyl-2-(2-methylprop-1-en-1-yl)benzamido]-2,3-dihydro-1H-indene-2-carboxylic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture 2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (134) (283 mg, 0.75 mmol) and KOH (600 mg, 10.7 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. The precipitate is filtered to give a pure product (135) as white solid (250 mg, 95%).

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. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-ac348d171fce48a78ab981d73dd58392
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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