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

HRID 2071690Notes

Reaction equation

HRID 2071690 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]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:8].Cl>[OH-].[Na+]>[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]([C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21411899HCID 21411899, compound

Product 1

HCID 21411918[4-Bromo-1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 2.6 g. (0.0715 mole) of ethyl 4-bromo-1-methyl-5-(p-toluoyl)pyrrole-2-acetate in 14.4 ml of 0.5N sodium hydroxide solution is heated under reflux for 30 minutes. It is then poured into dilute hydrochloride acid and the precipitated solid is filtered and air dried. Recrystallization of this precipitate from ether by addition of cyclohexane and evaporation of the ether until crystallization occurs yields as a white solid 4-bromo-1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid; m.p. 155°-157° C.

Workup

  1. additionA suspension of 2.6 g
  2. temperatureunder reflux for 30 minutes
  3. filtrationthe precipitated solid is filtered
  4. customair dried
  5. customRecrystallization of this precipitate from ether
  6. additionby addition of cyclohexane and evaporation of the ether
  7. customuntil crystallization

Sources & evidence

ORD record
ord-ea6a540cbaec42d1bd243f04bda1a6ec
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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