3-Nitro-pyridine-2,4-dicarboxylic acid diethyl ester → Diethyl 3-aminopyridine-2,4-dicarboxylate

HRID 59956Notes

Reaction equation

HRID 59956 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([N+:12]([O-])=O)=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:8][N:7]=1)=[O:5])[CH3:2]>[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 901905833-Nitro-pyridine-2,4-dicarboxylic acid diethyl ester

Product 1

HCID 90190411Diethyl 3-aminopyridine-2,4-dicarboxylateYield 69.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 3-Nitro-pyridine-2,4-dicarboxylic acid diethyl ester (55.00 g; 0.19 mol) was added Palladium on carbon (10% w/w) (6.00 g; 0.01 mol). The mixture was stirred at room temperature for 4 hours under 5 Kg of hydrogen pressure. After completion of the reaction, the reaction mixture was filtered through celite and the filtrate concentrated under vacuum. The residue was purified by column chromatography (60-120 mesh) using 15-20% EtOAc: petroleum ether to afford the title compound as a yellow solid (yield 69.7%). LC-MS [239 (M+H)], 1H NMR (400 MHz, DMSO-d6), 7.94-7.93 (d, 1H), 7.84-7.83 (d, 1H), 4.34-4.27 (m, 4H), 1.33-1.29 (m, 6H)

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe residue was purified by column chromatography (60-120 mesh)

Sources & evidence

ORD record
ord-1473b15419bc4804a662894e18534533
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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