N-(4-methyl-5-nitropyridin-2-yl)acetamide → N-(5-Amino-4-methylpyridin-2-yl)acetamide

HRID 1828541

Reaction equation

HRID 1828541 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1>C(O)C.[Pd]>[NH2:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([NH:11][C:12](=[O:14])[CH3:13])=[N:5][CH:6]=1

Participants

4

Reactant 1

HCID 13567013N-(4-methyl-5-nitropyridin-2-yl)acetamide2×

Product 1

HCID 22063573N-(5-Amino-4-methylpyridin-2-yl)acetamideYield 103%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The N1-(4-methyl-5-nitro-2-pyridyl)acetamide (4.70 g, 24.1 mmol) obtained in (A) was dissolved in ethanol (150 ml), added with 10% palladium/carbon (0.95 g) and subjected to catalytic reduction overnight at 1 atm under hydrogen atmosphere. The catalyst was removed by filtration and washed with ethanol. The filtrate was concentrated and the resulting residue was purified by silica gel column chromatography (chloroform chloroform:methanol=100:5) to obtain the title compound (4.10 g, quantitative) as brown solid.

Workup

  1. customsubjected to catalytic reduction overnight at 1 atm under hydrogen atmosphere
  2. customThe catalyst was removed by filtration
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. customthe resulting residue was purified by silica gel column chromatography (chloroform chloroform:methanol=100:5)

Sources & evidence

ORD record
ord-ef9681cf549f4b29a9a1e54462238dc5
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Linked notes

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