Ethyl Acetate → 5-Amino-4-methylpyridine-2-carbonitrile

HRID 1512979Notes

Reaction equation

HRID 1512979 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-])=O)=[CH:5][N:4]=1)#[N:2].[Cl-].[NH4+].C(OCC)(=O)C>O.[Zn]>[NH2:10][C:6]1[C:7]([CH3:9])=[CH:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 230001714-Methyl-5-nitropyridine-2-carbonitrile

Product 1

HCID 552898215-Amino-4-methylpyridine-2-carbonitrileYield 46.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

To a suspension of 2-cyano-4-methyl-5-nitropyridine (1.86 g) and ammonium chloride (3.05 g) in water (50 mL) was added zinc (7.46 g) under ice-cooling over 10 minutes, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added ethyl acetate (50 mL), and the resulting mixture was stirred at room temperature for 30 minutes. The insoluble material was removed by filtration, and the organic layer of the filtrate was separated. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residual solids were suspended in a mixed solvent (n-hexane/ethyl acetate=1/1), and collected by filtration. The collected solids were dried under reduced pressure to give the title compound (0.7 g).

Workup

  1. temperaturecooling over 10 minutes
  2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  3. customThe insoluble material was removed by filtration
  4. customthe organic layer of the filtrate was separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. filtrationcollected by filtration
  9. customThe collected solids were dried under reduced pressure

Sources & evidence

ORD record
ord-42cc8d3c11264404811a0f8d1496e31c
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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