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

HRID 1368411Notes

Reaction equation

HRID 1368411 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-8fc78afa6cd84ed8bd70abc8b679ffb4
Source dataset
uspto-grants-2003_06
Patent number
US06573293B2

Reaction notes

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