Water → 5-Benzoyl-1-methylpyrrole-2-acetic acid

HRID 1606135Notes

Reaction equation

HRID 1606135 reaction equation
[C:1]([C:9]1[N:13]([CH3:14])[C:12]([CH2:15][C:16]#N)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:18].[Na+].[OH2:20]>C(O)C>[C:1]([C:9]1[N:13]([CH3:14])[C:12]([CH2:15][C:16]([OH:20])=[O:18])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 184243635-Benzoyl-1-methylpyrrole-2-acetonitrile

Product 1

HCID 102638055-Benzoyl-1-methylpyrrole-2-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2.42 g. (0.11 mole) of 5-benzoyl-1-methylpyrrole-2-acetonitrile, 0.9 g. (0.22 mole) sodium hydroxide, 6 ml. water, and 0.5 ml. ethanol, is stirred and refluxed for one hour. The resulting solution is cooled and extracted in water and chloroform. The aqueous fraction is made acidic with 3N hydrochloric acid. A white solid, 5-benzoyl-1-methylpyrrole-2-acetic acid, precipitates which is filtered and washed with a hexane-ether solution, m.p. 144°-145°C.

Workup

  1. additionA suspension of 2.42 g
  2. temperaturerefluxed for one hour
  3. temperatureThe resulting solution is cooled
  4. extractionextracted in water
  5. customA white solid, 5-benzoyl-1-methylpyrrole-2-acetic acid, precipitates which
  6. filtrationis filtered
  7. washwashed with a hexane-ether solution, m.p. 144°-145°C.

Sources & evidence

ORD record
ord-edbae96204744e5e84379389b180c536
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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