Water → 4-(4-Chlorophenyl)-1H-pyrrole-2-carboxylic acid

HRID 1703309Notes

Reaction equation

HRID 1703309 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:13]([O:15]CCO)=[O:14])[NH:11][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[K+].O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[NH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 130642732-Hydroxyethyl 4-(4-chlorophenyl)pyrrole-2-carboxylate

Product 1

HCID 128970994-(4-Chlorophenyl)-1H-pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude 2-hydroxyethyl 4-(4-chlorophenyl)pyrrole-2-carboxylate (3 g.) was heated on a steam bath with potassium hydroxide (2 g.) in 25 ml. of water and 25 ml. of ethanol for 30 minutes. The balance of the ethanol was evaporated in vacuo, chloroform (25 ml.) was added and 4-(4-chlorophenyl)pyrrole-2-carboxylic acid (723 mg., m.p. 219°-222° C., ir(KBr): 3390, 3077 and 1695 cm.-1, m/e 221/223) recovered by filtration.

Workup

  1. customThe balance of the ethanol was evaporated in vacuo, chloroform (25 ml.)
  2. additionwas added
  3. filtration4-(4-chlorophenyl)pyrrole-2-carboxylic acid (723 mg., m.p. 219°-222° C., ir(KBr): 3390, 3077 and 1695 cm.-1, m/e 221/223) recovered by filtration

Sources & evidence

ORD record
ord-9e9a442533444dce9e366863366edc97
Source dataset
uspto-grants-1982_09
Patent number
US04351843

Reaction notes

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