Water → 5-Fluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid

HRID 1047789Notes

Reaction equation

HRID 1047789 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[CH:25]=[C: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[CH:25]=[C:26]([CH3:27])[CH3:28])([C:4]([OH:5])=[O:3])[CH2:14]2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314324HCID 59314324, compound

Product 1

HCID 251607995-Fluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acidYield 101%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture 5-fluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (148) (245 mg, 0.62 mmol) and KOH (600 mg, 10.7 mmol) is dissolved in EtOH (10 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 3 h. After concentration in vacuo, the residue is dissolved in water (30 mL) and acidified with conc. HCl until no more precipitate came out of the water. The precipitate is filtered to give a pure product (149) as white solid (230 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 (30 mL)
  6. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-335a7aba2cb44226a94e88c957173b86
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…