Acetic Acid → 5-(2-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 1707087Notes

Reaction equation

HRID 1707087 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=C(C#N)[C:11](=[O:14])[NH:12][CH:13]=1.Cl.[C:18]([OH:21])(=[O:20])[CH3:19]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:19]([C:18]([OH:21])=[O:20])[C:11](=[O:14])[NH:12][CH:13]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 136055345-(2-Chlorophenyl)-1,2-dihydro-2-oxo-3-pyridinecarbonitrile

Product 1

HCID 136055335-(2-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Procedure

A mixture of 19.0 g. of 5-(2-chlorophenyl)-1,2-dihydro-2-oxo-3-pyridinecarbonitrile and 1:1 concentrated hydrochloric acid and glacial acetic acid is heated at reflux temperature for 16 hours. A yellow solid is separated which is collected by filtration and is washed with water to give 18.4 g. of the product of the Example as yellow needles, m.p. 299°-303° C.

Workup

  1. additionA mixture of 19.0 g
  2. temperatureat reflux temperature for 16 hours
  3. customA yellow solid is separated which
  4. filtrationis collected by filtration
  5. washis washed with water
  6. customto give 18.4 g

Sources & evidence

ORD record
ord-04bb47998fde43f5986abbb1c4475282
Source dataset
uspto-grants-1980_06
Patent number
US04209626

Reaction notes

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