N-(2-methoxyphenyl)nicotinamide → HCID 13051663, compound

HRID 2199052Notes

Reaction equation

HRID 2199052 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])(=[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[O:16][CH3:17])(=[O:8])[C:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH:3]=1

Participants

5

Reactant 2

HCID 787042N-(2-methoxyphenyl)nicotinamideHCID 178418361HCID 178418361, compound

Product 1

HCID 13051663HCID 13051663, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Twenty-seven grams of N-nicotinoyl-2-methoxyaniline was dissolved in 800 ml of 10% hydrous ethanol. To the solution, 5 g of 10% palladium-on-carbon was added and the mixture was hydrogenated at 40° to 50° C. under atmospheric pressure. After 2 mols of hydrogen was introduced over a period of about 6 hours, the reaction was stopped and the catalyst was removed. The liquid reaction mixture was concentrated and the residual oil was purified with column chromatography on silica gel and recrystallized from hydrous methanol to give N-(1,4,5,6-tetrahydronicotinoyl)-2-methoxyaniline having a melting point of 126°-128° C. Yield=60%

Workup

  1. customwas hydrogenated at 40° to 50° C. under atmospheric pressure
  2. customthe catalyst was removed
  3. customThe liquid reaction mixture
  4. concentrationwas concentrated
  5. customthe residual oil was purified with column chromatography on silica gel
  6. customrecrystallized from hydrous methanol

Sources & evidence

ORD record
ord-da4f3b872a5b4eb3a35c013ef0ebc88a
Source dataset
uspto-grants-1982_11
Patent number
US04361572

Reaction notes

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