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

HRID 1282360Notes

Reaction equation

HRID 1282360 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-590e0da45915479eb13a4e5cbc7b7152
Source dataset
uspto-grants-2002_09
Patent number
US06455703B2

Reaction notes

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