n-Methyl-3-nitropyridin-4-amine → 4-N-methylpyridine-3,4-diamine

HRID 1751804Notes

Reaction equation

HRID 1751804 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[N+:9]([O-])=O.[H][H]>CO.[Ni]>[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[NH2:9]

Participants

5

Reactant 2

HCID 556016n-Methyl-3-nitropyridin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 9104124-N-methylpyridine-3,4-diamineYield 83.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

2.3 g methyl-(3-nitropyridin-4-yl)-amine are hydrogenated in 50 ml of methanol with 0.8 g Raney nickel for 2.5 h at 50° C. under 50 psi hydrogen pressure. The catalyst is filtered off and the filtrate is evaporated to dryness. The product is purified by chromatography (Alox, dichloromethane/methanol of 99/1 to 19/1). 1.55 g product are obtained in the form of a solid. m.p: 163-165° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated to dryness
  3. customThe product is purified by chromatography (Alox, dichloromethane/methanol of 99/1 to 19/1)

Sources & evidence

ORD record
ord-a1eeee049da64848af458b4129bc550e
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

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