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

HRID 1008149Notes

Reaction equation

HRID 1008149 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-467f21ed48bf443abb243962ad1bd802
Source dataset
uspto-grants-2004_09
Patent number
US06797725B2

Reaction notes

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