Hydrochloric Acid → 1,4-Dimethyl-5-(p-toluoyl)-pyrrole-2-acetic acid

HRID 1606172Notes

Reaction equation

HRID 1606172 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])=[C:5]([CH3:16])[CH:4]=[C:3]1[CH2:17][C:18]([O:20]CC)=[O:19].[OH-].[Na+].Cl>O>[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])=[C:5]([CH3:16])[CH:4]=[C:3]1[CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18424313Ethyl 1,4 dimethyl-5-(rho-toluoyl)-pyrrole-2-acetate

Product 1

HCID 185442751,4-Dimethyl-5-(p-toluoyl)-pyrrole-2-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 8.5 g. (0.0284 mole) of ethyl 1,4-dimethyl-5-(p-toluoyl)-pyrrole- 2-acetate in 29 ml. of 1N sodium hydroxide solution is heated under reflux for 20 min. The yellow solution is diluted with water and added to dilute hydrochloric acid. The precipitated solid is collected, dried in vacuo, and recrystallized from 2-propanol to give 1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetic acid as a white solid, m.p. 160°-161°C.

Workup

  1. additionA suspension of 8.5 g
  2. temperatureunder reflux for 20 min
  3. customThe precipitated solid is collected
  4. customdried in vacuo
  5. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-b3aa18e7dcae4b2aa559557e4c15135d
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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