N-(2-Fluorophenyl)pyridine-3-carboximidic acid → HCID 13051668, compound

HRID 2199053Notes

Reaction equation

HRID 2199053 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[C:1]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16])(=[O:8])[C:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH:3]=1

Participants

5

Reactant 2

HCID 279880N-(2-Fluorophenyl)pyridine-3-carboximidic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 13051668HCID 13051668, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Fifty grams of N-nicotinoyl-2-fluoroaniline was dissolved in 700 ml of 10% hydrous ethanol. To the solution, 5 g of 10% palladium-on-carbon was added and the mixture was reduced with hydrogen at room temperature and at atmospheric pressure. When a stoichiometric amount of hydrogen was absorbed, the reaction was stopped and the catalyst was removed. the liquid reaction mixture was concentrated and the resulting crystal was recrystallized from hydrous methanol to give N-(1,4,5,6-tetrahydronicotinoyl)-2-fluoroaniline having a melting point of 137° to 140° C. Yield=70%.

Workup

  1. customWhen a stoichiometric amount of hydrogen was absorbed
  2. customthe catalyst was removed
  3. customthe liquid reaction mixture
  4. concentrationwas concentrated
  5. customthe resulting crystal was recrystallized from hydrous methanol

Sources & evidence

ORD record
ord-927e2ec59bc546d49ae7bf3c3b1ab990
Source dataset
uspto-grants-1982_11
Patent number
US04361572

Reaction notes

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