Hydrochloric Acid → 5-Benzoyl-1-methylpyrrole-2-acetic acid

HRID 848044Notes

Reaction equation

HRID 848044 reaction equation
C([C:3]([OH:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4]1[N:8]([CH3:9])[C:7]([CH2:10][C:11]([O:13]C)=[O:12])=[CH:6][CH:5]=1)#N.Cl>[OH-].[Na+]>[C:3]([C:4]1[N:8]([CH3:9])[C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12940094Methyl 1-methyl-5-(cyanohydroxyphenylmethyl)pyrrole-2-acetate

Product 1

HCID 102638055-Benzoyl-1-methylpyrrole-2-acetic acidYield 77%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 1.0 g of methyl 5-(cyanohydroxyphenylmethyl)-1-methylpyrrole-2-acetate in 20 ml of 5 percent sodium hydroxide solution was heated under reflux for 30 minutes. The solution was acidified with 3 N hydrochloric acid solution. The solid was collected and recrystallized from acetonitrile to give 0.61 g (77 percent yield) of white crystalline 5-benzoyl-1-methylpyrrole-2-acetic acid, mp 145°-6°, undepressed by admixture with authentic product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customThe solid was collected
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-7efaf7d2dd0b4b96a71f3cb97e4cfb3c
Source dataset
uspto-grants-1981_10
Patent number
US04294760

Reaction notes

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