4,5-Diphenyl-1H-pyrrole-2,3-dicarboxylic acid → HCID 10104838, compound

HRID 2286579Notes

Reaction equation

HRID 2286579 reaction equation
[C:1]1([C:7]2[C:8](C(O)=O)=[C:9](C(O)=O)[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>N1C2C(=CC=CC=2)C=CC=1>[C:12]1([C:11]2[NH:10][CH:9]=[CH:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 155722434,5-Diphenyl-1H-pyrrole-2,3-dicarboxylic acid

Product 1

HCID 10104838HCID 10104838, compound

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent2×

Procedure

A mixture of 20 g (0.065 mole) of 4,5-diphenylpyrrole-2,3-dicarboxylic acid in 80 ml quinoline was heated at reflux in an oil bath (bath ~230°) until gas evolution stopped (approx. one-half hour). The reaction mixture was cooled and most of the quinoline was removed by distillation (bp 58° @ 0.2 mm). The partially crystalline residue was chromatographed on 300 g Silic AR CC-7, eluting with toluene to give 12 g (85%) of faintly pink 2,3-diphenylpyrrole which could be further purified by recrystallization from ethanol/water or by sublimation (~125° @ 0.2 mm) to give white solid, m.p. 132°-3°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in an oil bath (bath ~230°) until gas evolution
  3. custom(approx. one-half hour)
  4. customwas removed by distillation (bp 58° @ 0.2 mm)
  5. customThe partially crystalline residue was chromatographed on 300 g Silic AR CC-7
  6. washeluting with toluene

Sources & evidence

ORD record
ord-aba1be4791cb44879f3b5f89a3d7a6ae
Source dataset
uspto-grants-1981_05
Patent number
US04267184

Reaction notes

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