HCID 21411844, compound → [4-Bromo-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetic acid

HRID 2071687Notes

Reaction equation

HRID 2071687 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:17][C:18]([O:20]CC)=[O:19])[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-].[Na+].C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:17][C:18]([OH:20])=[O:19])[N:5]([CH3:16])[C:6]=1[C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1

Participants

5

Reactant 1

HCID 21411844HCID 21411844, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 0.9 g. of ethyl 4-bromo-5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetate in 5 ml of 0.5N sodium hydroxide solution containing a few drops of ethanol is heated under reflux for one hour. At the end of 1 hour it is cooled, diluted with water and filtered, and the filtrate washed with ether. The aqueous filtrate is then acidified with dilute hydrochloric acid and the resulting precipitated solid is collected and air dried. Recrystallization thereof from acetonitrile gives 4-bromo-5-(p-chlorobenzoyl)- 1-methylpyrrole-2-acetic acid as a pink solid; m.p. 190° C. (dec.)

Workup

  1. additionA suspension of 0.9 g
  2. temperatureis heated
  3. temperatureunder reflux for one hour
  4. temperatureAt the end of 1 hour it is cooled
  5. filtrationfiltered
  6. washthe filtrate washed with ether
  7. customthe resulting precipitated solid
  8. customis collected
  9. customair dried
  10. customRecrystallization

Sources & evidence

ORD record
ord-b44059f724d6403aba81c9e589b6ea72
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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