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

HRID 1733570Notes

Reaction equation

HRID 1733570 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-e15fd66cfc4342cc9fa3ccf24d1dadcc
Source dataset
uspto-grants-1980_12
Patent number
US04242515

Reaction notes

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