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

HRID 1606170Notes

Reaction equation

HRID 1606170 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 min. 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 min
  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-59addbbe0e9e4cabb1761379a67184ba
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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