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

HRID 1275295Notes

Reaction equation

HRID 1275295 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 minutes. 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. Anal. Calcd. for C16H17NO3 : C, 70.83; H, 6.32; N, 5.16%. Found: C, 70.90; H, 6.39; N, 5.25%.

Workup

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

Sources & evidence

ORD record
ord-6b051158c7d74603bb88b4b27c801307
Source dataset
uspto-grants-2000_12
Patent number
US06160003

Reaction notes

Loading…