Water → 5-Fluoro-2-(2-isopropoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047750Notes

Reaction equation

HRID 1047750 reaction equation
C([O:3][C:4]([C:6]1([NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=2[O:25][CH:26]([CH3:28])[CH3:27])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:15])[CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[F:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:16][C:17](=[O:29])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[O:25][CH:26]([CH3:27])[CH3:28])([C:4]([OH:5])=[O:3])[CH2:14]2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593144025-Fluoro-2-(2-isopropoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 251605405-Fluoro-2-(2-isopropoxy-3-methyl-benzoylamino)-indan-2-carboxylic acidYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 5-fluoro-2-(2-isopropoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (96) (544 mg, 1.36 mmol) and KOH (1 g, 18 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 8 h. After concentration in vacuo, the residue is dissolved in water (30 mL) and acidified with conc. HCl until no more white precipitate formed. The precipitate is filtered to give a pure product (97) as white solid (460 mg, 91%).

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 (30 mL)
  6. customformed
  7. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-3a9055b1ba5a4610b490db974017baa4
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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