Water → HCID 59314186, compound

HRID 1047696Notes

Reaction equation

HRID 1047696 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:26]3[O:25][CH2:24][CH2:23][C:22]=3[CH:21]=[CH:20][CH:19]=2)=[O:17])[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>[O:25]1[C:26]2[C:18]([C:16]([NH:15][C:6]3([C:4]([OH:5])=[O:3])[CH2:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:7]3)=[O:17])=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314300HCID 59314300, compound

Product 1

HCID 59314186HCID 59314186, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-[(2,3-Dihydro-benzofuran-7-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (39) (250 mg, 0.71 mmol) and KOH (600 mg, 10.7 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 overnight. After concentration in vacuo, the residue is dissolved in water (30 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 (40) as white solid (200 mg, 87%).

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-bb33664176aa4c9192c8b871c5a6a2f8
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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