Hydrochloric Acid → 3-Carboxy-1,4-dimethyl-1H-pyrrole-2-acetic acid

HRID 1606177Notes

Reaction equation

HRID 1606177 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[C:4]([C:8]([O:10]CC)=[O:9])=[C:3]1[CH2:13][C:14]([O:16]CC)=[O:15].[OH-].[Na+].Cl>>[C:8]([C:4]1[C:5]([CH3:7])=[CH:6][N:2]([CH3:1])[C:3]=1[CH2:13][C:14]([OH:16])=[O:15])([OH:10])=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118460Ethyl 3-(ethoxycarbonyl)-1,4-dimethyl-1H-pyrrole-2-acetate

Product 1

HCID 1184653-Carboxy-1,4-dimethyl-1H-pyrrole-2-acetic acidYield 98%

Procedure

A mixture of 176 g. (0.7 mole) of ethyl 1,4-dimethyl-3-ethoxycarbonylpyrrole-2-acetate and 1760 ml. of 25% sodium hydroxide solution is heated under reflux for 3 hr. and then cooled and acidified with dilute hydrochloric acid. The precipitated solid is filtered and air dried. There is obtained 130 g. (98% yield) of 3-carboxy-1,4-dimethylpyrrole-2-acetic acid as a gray solid, m.p. 220°-222°C.

Workup

  1. additionA mixture of 176 g
  2. temperatureunder reflux for 3 hr
  3. temperatureand then cooled
  4. filtrationThe precipitated solid is filtered
  5. customair dried
  6. customThere is obtained 130 g

Sources & evidence

ORD record
ord-3fbd1782207144a482a7edefda8dea9c
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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