5-Nitropyridine-2,4-diamine → Pyridine-2,4,5-triamine

HRID 854080Notes

Reaction equation

HRID 854080 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>CCO.[Ni]>[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 218138965-Nitropyridine-2,4-diamine

Product 1

HCID 21813897Pyridine-2,4,5-triamineYield 98.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 5 (0.540 g, 3.5 mmol) in EtOH (50 ml) and Raney Nickel (0.600 ml) was stirred under H2 atmosphere for 3 h at room temperature. The product was freed from catalyst by filtration through celite to give 6 (0.428 g, 98%); 1H NMR (DMSO-d6, 500 MHz): δ 7.11 (1H, s), 5.65 (1H, s) 5.12 (2H, brs), 4.64 (2H, brs) 3.34 (2H, brs); EIMS m/z: 125 (M+1) and used as is in the next step.

Workup

  1. filtrationThe product was freed from catalyst by filtration through celite

Sources & evidence

ORD record
ord-a2474a818ea841cfbe35581677ca9921
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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