Water → [4-Chloro-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetic acid

HRID 2071682Notes

Reaction equation

HRID 2071682 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:17][C:18]#N)[N:5]([CH3:16])[C:6]=1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[OH-:20].[Na+].[OH2:22]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:17][C:18]([OH:22])=[O:20])[N:5]([CH3:16])[C:6]=1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21411896[4-Chloro-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetonitrile

Product 1

HCID 21411858[4-Chloro-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.3 g. (0.015 mole) of 4-chloro-5- (p-chlorobenzoyl)-1-methylpyrrole-2-acetonitrile and 1.2 g. (0.030 mole) of sodium hydroxide in 11 ml. of deionized water and 20 ml. of 95% ethanol is stirred and refluxed for seven hours and is then stirred at ambient temperature for about 18 hours. The precipitate which results when this reaction mixture is poured into 500 ml. of dilute hydrochloric acid is filtered off, washed with water, and recrystallized once from acetonitrile and once from diethyl ether in a Soxhlet extractor to give 4-chloro-5-(p-chlorobenzoyl)-1- methylpyrrole-2-acetic acid as a buff solid; m.p. 203°-204° C. (dec.)

Workup

  1. temperaturerefluxed for seven hours
  2. customThe precipitate which results when this reaction mixture
  3. additionis poured into 500 ml
  4. filtrationof dilute hydrochloric acid is filtered off
  5. washwashed with water
  6. customrecrystallized once from acetonitrile and once from diethyl ether in a Soxhlet extractor

Sources & evidence

ORD record
ord-355801713ae241fc9075d1d4a23a74f0
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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