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

HRID 1282362Notes

Reaction equation

HRID 1282362 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-228ae9a4445140ceb4c5258e1dffb7ce
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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