6-Methyl-5-nitropyridin-2-amine → 6-methylpyridine-2,5-diamine

HRID 1378434Notes

Reaction equation

HRID 1378434 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([CH3:11])[N:3]=1>[Pd].CCO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:11])[N:3]=1

Participants

4

Reactant 1

HCID 2479766-Methyl-5-nitropyridin-2-amine

Product 1

HCID 27344216-methylpyridine-2,5-diamineYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-nitro-6-methylpyridine (5.42 g, 0.0354 mol) (E. D. Parker and W. Shive, J. Amer. Chem. Soc., 69:63 (1947)), absolute EtOH (150 ml) and 10% palladium-on-carbon catalyst (0.488 g) was hydrogenated at an initial pressure of 40 p.s.i. for 18 hours. The catalyst was removed by filtration through celite and the filtrate was concentrated to give 4.34 g of the titled product.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-643c97ac04f84a5ea74de4b44a3cd338
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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