Diethyl 6-amino-5-nitro-2,3-pyridinedicarboxylate → Diethyl 5,6-diamino-2,3-pyridinedicarboxylate

HRID 864899Notes

Reaction equation

HRID 864899 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:3]=1[N+:18]([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:18][C:3]1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:7][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 21847045Diethyl 6-amino-5-nitro-2,3-pyridinedicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 21847042Diethyl 5,6-diamino-2,3-pyridinedicarboxylateYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl 6-amino-5-nitro-2,3-pyridinedicarboxylate (5.00 g,. 0.0176 tool) is suspended in 250 mL of absolute ethanol and the mixture cooled to 0° C. Palladium on carbon (50 g of 10% is added and the mixture is shaken under 50 psi hydrogen in a Parr apparatus for four hours. The catalyst is removed by filtration through a pad of Celite, and the filtrate is concentrated to yield 4.21 g (94.2%) of product as a yellow solid, melting point 143°-146.5° C.

Workup

  1. customThe catalyst is removed by filtration through a pad of Celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-3ec15e3973e44644a55d385717934324
Source dataset
uspto-grants-1996_10
Patent number
US05565411

Reaction notes

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