Sodium Hydroxide → HCID 12897086, compound

HRID 1980941Notes

Reaction equation

HRID 1980941 reaction equation
[C:1]1([C:7]2[C:8]([C:20]([O:22]C)=[O:21])=[CH:9][NH:10][C:11]=2[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]2[C:8]([C:20]([OH:22])=[O:21])=[CH:9][NH:10][C:11]=2[C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12897085HCID 12897085, compound

Product 1

HCID 12897086HCID 12897086, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-phenyl-5-benzoylpyrrole-3-carboxylate (345 mg.) was combined with 20 ml. of methanol and 10 ml. of 1N sodium hydroxide and boiled in an open flask for 1 hour. The aqueous residue was cooled, extracted with ethyl acetate, acidified with conc. hydrochloric acid, and product recovered by filtration. Recrystallization from tetrahydrofuran/hexane afforded purified 4-phenyl-5-benzoylpyrrole-3-carboxylic acid [63 mg., m.p. 285°-287° C. (dec.)].

Workup

  1. temperatureThe aqueous residue was cooled
  2. extractionextracted with ethyl acetate
  3. filtrationrecovered by filtration
  4. customRecrystallization from tetrahydrofuran/hexane
  5. customafforded
  6. custompurified 4-phenyl-5-benzoylpyrrole-3-carboxylic acid [63 mg., m.p. 285°-287° C. (dec.)]

Sources & evidence

ORD record
ord-cd268e7a495c4badab58f0dc19f82e35
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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