Water → 2-(3-Methyl-2-pentyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047768Notes

Reaction equation

HRID 1047768 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[CH2:24][CH2:25][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]([CH2:24][CH2:25][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 593144082-(3-Methyl-2-pentyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593142372-(3-Methyl-2-pentyl-benzoylamino)-indan-2-carboxylic acidYield 101.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(3-methyl-2-pentyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (126) (68 mg, 0.17 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 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 (127) as a pale brown solid (63 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-ccb6920caa3740e7abc6cdb8484e6100
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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