Water → HCID 59314309, compound

HRID 1047706Notes

Reaction equation

HRID 1047706 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N: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>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:14]2)=[O:17])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314392HCID 59314392, compound

Product 1

HCID 59314309HCID 59314309, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-[(quinoline-4-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (49) (220 mg, 0.61 mmol) and KOH (600 mg, 10.7 mmol) is dissolved in EtOH (10 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˜4. The precipitate is filtered to give a pure product (50) as a pale yellow solid (98 mg, 48%).

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-b090367dc50d45fe9b155d5ad75c9bcd
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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