Potassium Hydroxide → 5-(5-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid

HRID 2252125Notes

Reaction equation

HRID 2252125 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:12]=[C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[NH:15][C:14]2=[O:23])=[C:9]([CH3:11])[CH:10]=1)=[O:5])C.[OH-].[K+]>CO.C(O)C>[Cl:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:23])[C:13]2=[CH:12][C:8]1[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][C:9]=1[CH3:11]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 672810735-(5-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 672812935-(5-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acidYield 72.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 5-(5-chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.3 g, 4 mmol) and potassium hydroxide in methanol (25 mL) and ethanol (25 mL) was heated to reflux for overnight. Insoluble materials were removed by filtration and the mixture was neutralized with 6N hydrochloric acid to give 0.876 g (70%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. customInsoluble materials were removed by filtration

Sources & evidence

ORD record
ord-927eb4a83fef463088cffcfea41d0a3f
Source dataset
uspto-grants-2008_01
Patent number
US07320996B2

Reaction notes

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