Water → 2-(2-Allyloxy-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047662Notes

Reaction equation

HRID 1047662 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[O:24][CH2:25][CH:26]=[CH2:27])[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>[CH2:25]([O: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])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:28])[CH:26]=[CH2:27]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593142442-(2-Allyloxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593142842-(2-Allyloxy-3-methyl-benzoylamino)-indan-2-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(2-allyloxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (4) (168 mg, 0.44 mmol) and KOH (500 mg, 8.9 mmol) is dissolved in EtOH (5 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 white precipitate came out of the water. The precipitate is filtered to give a pure product (5) as white solid (150 mg, 97%).

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-000f79ab44fb4ff38406985b35cc0727
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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