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

HRID 1047670Notes

Reaction equation

HRID 1047670 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[O:24][CH:25]([CH2:27][CH3:28])[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>[CH: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])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:29])([CH2:27][CH3:28])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593141082-(2-sec-Butoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 251602812-(2-sec-Butoxy-3-methyl-benzoylamino)-indan-2-carboxylic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(2-sec-butoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (12) (176 mg, 0.44 mmol) and KOH (500 mg, 8.93 mmol) is dissolved in EtOH (6 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 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 (13) as white solid (162 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-7c24c4e331b84971a4e442f0e6717448
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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