Quinoline → 5-(4-Chlorophenyl)-2-hydroxypyridine

HRID 1707088

Reaktionsgleichung

Reaktionsgleichung von HRID 1707088
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10](C(O)=O)[C:11](=[O:14])[NH:12][CH:13]=2)=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=2)=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 7047QuinolineHCID 100149755-(4-Chlorophenyl)-2-hydroxynicotinic acid

Produkt 1

HCID 102623725-(4-Chlorophenyl)-2-hydroxypyridine

Versuchsvorschrift

A mixture of 40.0 g. of 5-(4-chlorophenyl)-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid (prepared as described in Example 12) and 120 ml. of quinoline is heated at reflux temperature for 4 hours. The mixture is cooled and filtered. The solid is washed with ether and then is dissolved in chloroform. The chloroform solution is treated with activated charcoal and is filtered. The filtrate is concentrated and diluted with hexane yielding 22.0 g. of the product of the Example as a tan solid. The solid is recrystallized from chloroform-hexane to give tan crystals, m.p. 183°-185.5° C.

Aufarbeitung

  1. additionA mixture of 40.0 g
  2. temperatureat reflux temperature for 4 hours
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. washThe solid is washed with ether
  6. dissolutionis dissolved in chloroform
  7. additionThe chloroform solution is treated with activated charcoal
  8. filtrationis filtered
  9. concentrationThe filtrate is concentrated
  10. additiondiluted with hexane yielding 22.0 g
  11. customThe solid is recrystallized from chloroform-hexane
  12. customto give tan crystals, m.p. 183°-185.5° C.

Quellen und Nachweise

ORD-Eintrag
ord-466884aae3ef49c8b1ec9f83e87a6f3d
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04209626

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