Methyl 6-amino-5-nitropyridine-3-carboxylate → Methyl 5,6-diaminopyridine-3-carboxylate

HRID 1638586Notes

Reaction equation

HRID 1638586 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1>CO.[C].[Pd]>[NH2:12][C:11]1[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 13768248Methyl 6-amino-5-nitropyridine-3-carboxylate

Product 1

HCID 9920476Methyl 5,6-diaminopyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1 Gram of methyl 6-amino-5-nitronicotinate was dissolved in 10 m of methanol. To this solution was added 0.1 g of 5%-palladium-carbon, then hydrogen gas was absorbed at room temperature under a normal pressure. The reaction was stopped when the stoichiometric amount of hydrogen was absorbed. The catalyst was removed from the reaction mixture by filtration, and the solvent was removed by evaporation. The residue thus obtained was recrystallized from ethanol to yield 0.8 g of methyl 5,6-diaminonicotinate in the form of yellow needle-like crystals. Melting point: 154°-155° C.

Workup

  1. customhydrogen gas was absorbed at room temperature under a normal pressure
  2. customwas absorbed
  3. customThe catalyst was removed from the reaction mixture by filtration
  4. customthe solvent was removed by evaporation
  5. customThe residue thus obtained
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-945a1ec7ff7440ebb49d454240d904d5
Source dataset
uspto-grants-1989_11
Patent number
US04880815

Reaction notes

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