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

HRID 863645Notes

Reaction equation

HRID 863645 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-(ρ-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-(ρ-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-d92df6b78ca84ed5bb8c7785f42cb774
Source dataset
uspto-grants-1998_02
Patent number
US05721347

Reaction notes

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