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

HRID 1585613Notes

Reaction equation

HRID 1585613 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-7efc3fbfe9af43ba9ec5359901e63257
Source dataset
uspto-grants-1999_08
Patent number
US05939417

Reaction notes

Loading…