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

HRID 1047675Notes

Reaction equation

HRID 1047675 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]([Cl: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]([Cl: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 593142682-(2-Allyloxy-3-chloro-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 593143912-(2-Allyloxy-3-chloro-benzoylamino)-indan-2-carboxylic acidYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(2-allyloxy-3-chloro-benzoylamino)-indan-2-carboxylic acid ethyl ester (17) (140 mg, 0.35 mmol) and KOH (500 mg, 8.9 mmol) is dissolved in EtOH (5 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 pH˜3. After filtration, the solid is purified by HPLC to give a pure product (18) as white solid (88 mg, 68%).

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. filtrationAfter filtration
  7. customthe solid is purified by HPLC

Sources & evidence

ORD record
ord-c4a24a68d5404846936a10a08f6fa8c4
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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