Ethanol → 6-(4-Chlorophenyl)pyridine-3-carboxamide

HRID 1980329Notes

Reaction equation

HRID 1980329 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.OO.[OH-].[Na+].C([OH:22])C>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]([NH2:15])=[O:22])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 148232346-(4-Chlorophenyl)pyridine-3-carbonitrile

Product 1

HCID 135028606-(4-Chlorophenyl)pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-(4-Chlorophenyl)-3-pyridinecarbonitrile (1.61 grams), 30% hydrogen peroxide (3.0 cc.), 6N sodium hydroxide (0.3 cc.), and about 6 ml ethanol were placed in a reaction vessel and cooled slightly. The reaction temperature rose to about 50° C. and the mixture was stirred for about 1 hour. After the reaction had cooled, a solid precipitate formed and was collected by filtration. As indicated by TLC, pure product was obtained by heating the solid in refluxing acetone, yield 0.4 gram, m.p. 245°-258° C.

Workup

  1. temperaturecooled slightly
  2. customrose to about 50° C.
  3. temperatureAfter the reaction had cooled
  4. customa solid precipitate formed
  5. filtrationwas collected by filtration
  6. custompure product was obtained
  7. temperatureby heating the solid

Sources & evidence

ORD record
ord-d8c1de284f5d40ea924dc294833c180c
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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