Hydrochloric Acid → 3-Chloro-4-(2,3-dichlorophenyl)-1H-pyrrole

HRID 2286127Notes

Reaction equation

HRID 2286127 reaction equation
[Cl:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[Cl:20])=[C:4](C(O)=O)[NH:5][C:6]=1C(O)=O.N1C2C(=CC=CC=2)C=CC=1.Cl>C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[Cl:20])=[CH:4][NH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7047Quinoline2×HCID 12832894HCID 12832894, compound

Product 1

HCID 128838083-Chloro-4-(2,3-dichlorophenyl)-1H-pyrroleYield 84.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 53 g of 4-chloro-3-(2,3-dichlorophenyl)pyrol-2,5-dicarboxylic acid, 2.65 g of cupric acid and 80 ml of quinoline was heated at 140°-150° C. for 30 minutes with stirring. To the resulting reaction mixture were added ethyl acetate, ice and concentrated hydrochloric acid which of molar amount was 1.1-time that of employed quinoline. The ethyl acetate layer was washed with successive, water, aqueous sodium carbonate and water. After dehydration, the ethyl acetate layer was evaporated to dryness under reduced pressure to obtain 33.1 g of brown product. The crude product was purified by silicagel chromatography and countercurrent distribution to obtain pale yellow oily substance. The oily substance was recrystallized from n-hexane to obtain 22.5 g of the desired product (colorless or pale yellow needles, m.p. 58°-59° C.).

Workup

  1. temperaturewas heated at 140°-150° C. for 30 minutes
  2. customTo the resulting reaction mixture
  3. washThe ethyl acetate layer was washed with successive, water, aqueous sodium carbonate and water
  4. customAfter dehydration, the ethyl acetate layer was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8f8ab44583774f2094fe7505da4d4542
Source dataset
uspto-grants-1982_04
Patent number
US04326881

Reaction notes

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