Hydrochloric Acid → (1,4-Dimethyl-1H-pyrrol-2-yl)acetic acid

HRID 894470Notes

Reaction equation

HRID 894470 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[CH2:8][C:9]([O:11]CC)=[O:10].Cl.N1C=CC=C1CC(O)=O>[OH-].[Na+]>[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetateHCID 42201462-(1H-pyrrol-2-yl)acetic Acid

Product 1

HCID 3018854(1,4-Dimethyl-1H-pyrrol-2-yl)acetic acidYield 89%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A reference sample of 1,4-dimethylpyrrole-2-acetic acid was prepared as follows: A 9.05 g sample of ethyl 1,4-dimethylpyrrole-2-acetate [J. R. Carson and S. Wong, J. Med. Chem., 16, 172 (1973)] was heated under reflux with 30 ml of 10% sodium hydroxide solution for one hour. The solution was acidified with dilute HCl and extracted with ether. The ether was washed with brine and dried (MgSO4). The solvent was evaporated in vacuo and the residue was triturated with hexane and collected by filtration to give 6.8 g (89% yield) of 1,4-dimethylpyrrole-2-acetic acid as a pink crystalline solid, mp 86°-7° C. (d).

Workup

  1. customA reference sample of 1,4-dimethylpyrrole-2-acetic acid was prepared
  2. extractionextracted with ether
  3. washThe ether was washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was triturated with hexane
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5ba76f8e9d814c9499492b1f8b90a9d8
Source dataset
uspto-grants-1981_08
Patent number
US04284562

Reaction notes

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