Hydrochloric Acid → Ethyl 3-carboxy-1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetate

HRID 1275293Notes

Reaction equation

HRID 1275293 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[O:11])[N:6]([CH3:19])[C:5]=1[CH2:20][C:21]([OH:23])=[O:22])([OH:3])=[O:2].Cl.[CH2:25](O)[CH3:26]>>[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[O:11])[N:6]([CH3:19])[C:5]=1[CH2:20][C:21]([O:23][CH2:25][CH3:26])=[O:22])([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 184243523-Carboxy-1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetic acid

Product 1

HCID 18424327Ethyl 3-carboxy-1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetate

Procedure

A solution of 37 g. (0.118 mole) of 3-carboxy-1,4-dimethyl-5-(p-toluoyl)-pyrrole-2-acetic acid in 370 ml. of ethanol containing 1.8 g. of dry hydrogen chloride is heated under reflux for 45 minutes. The solution is cooled, and the solid which precipitated, ethyl 3-carboxy-1,4-dimethyl-5-(o-toluoyl)-pyrrole-2-acetate, is collected, m.p. 200-202° C.

Workup

  1. temperatureunder reflux for 45 minutes
  2. temperatureThe solution is cooled
  3. customthe solid which precipitated
  4. customethyl 3-carboxy-1,4-dimethyl-5-(o-toluoyl)-pyrrole-2-acetate, is collected

Sources & evidence

ORD record
ord-dbf0c41510694d9e87f1236bd6f5be46
Source dataset
uspto-grants-2000_12
Patent number
US06160003

Reaction notes

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