Ethyl 5-(4-phenylbenzoyl)pyrrole-3-carboxylate → 5-(4-Phenylbenzoyl)pyrrole-3-carboxylic Acid

HRID 1981011Notes

Reaction equation

HRID 1981011 reaction equation
[C:1]1([C:7]2[CH:24]=[CH:23][C:10]([C:11]([C:13]3[NH:17][CH:16]=[C:15]([C:18]([O:20]CC)=[O:19])[CH:14]=3)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:11]([C:13]3[NH:17][CH:16]=[C:15]([C:18]([OH:20])=[O:19])[CH:14]=3)=[O:12])=[CH:23][CH:24]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 12897070Ethyl 5-(4-phenylbenzoyl)pyrrole-3-carboxylate

Product 1

HCID 128970715-(4-Phenylbenzoyl)pyrrole-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 5-(4-phenylbenzoyl)pyrrole-3-carboxylate (3.1 g.) was boiled in an open flask with 100 ml. of methanol and 70 ml. of 1N sodium hydroxide for 1 hour by which time most of the methanol was removed by evaporation. The solution was cooled to room temperature, and product which had precipitated as the sodium salt recovered by filtration. The salt was stirred with 75 ml. of 1N hydrochloric acid and 5-(4-phenylbenzoyl)pyrrole-3-carboxylic acid (1 g., m.p.>280° C.) recovered by filtration.

Workup

  1. customof 1N sodium hydroxide for 1 hour by which time most of the methanol was removed by evaporation
  2. customproduct which had precipitated as the sodium salt
  3. filtrationrecovered by filtration
  4. filtrationof 1N hydrochloric acid and 5-(4-phenylbenzoyl)pyrrole-3-carboxylic acid (1 g., m.p.>280° C.) recovered by filtration

Sources & evidence

ORD record
ord-7aee9e309eec471993839f29927e2048
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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