Hydrochloric Acid → [4-Bromo-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetic acid

HRID 2071695Notes

Reaction equation

HRID 2071695 reaction equation
[OH-:1].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:19][C:20]#N)[N:7]([CH3:18])[C:8]=1[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1.Cl.[OH2:23]>C(O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH2:19][C:20]([OH:23])=[O:1])[N:7]([CH3:18])[C:8]=1[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 21411961[4-Bromo-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetonitrile

Product 1

HCID 21411835[4-Bromo-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.05 g (1.1 m mole) of sodium hydroxide in 2 ml of water and 2 ml of ethanol is combined with 0.19 g (0.56 m mole) of 4bromo-5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetnitrile, and the whole is stirred and refluxed for 4 hours. The resulting mixture is poured into 30 ml of cold 3N hydrochloric acid; the precipitate which forms is filtered off and washed well with water. Recrystallization of this precipitate from acetonitrile yields 4-bromo-5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetic acid as a pink solid; m.p. 190° C. (dec.)

Workup

  1. temperaturerefluxed for 4 hours
  2. filtrationthe precipitate which forms is filtered off
  3. washwashed well with water
  4. customRecrystallization of this precipitate from acetonitrile

Sources & evidence

ORD record
ord-891590bda26744659f5c7bc0d3cacd7b
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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