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

HRID 1703290Notes

Reaction equation

HRID 1703290 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 1 N 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 1 N hydrochloric acid and 5-(4-phenylbenzoyl)pyrrole-3-carboxylic acid (1 g., m.p. >280° C.) recovered by filtration.

Workup

  1. customof 1 N 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 1 N hydrochloric acid and 5-(4-phenylbenzoyl)pyrrole-3-carboxylic acid (1 g., m.p. >280° C.) recovered by filtration

Sources & evidence

ORD record
ord-7ede9f5274a948478509f4650e674060
Source dataset
uspto-grants-1982_09
Patent number
US04351843

Reaction notes

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