2-Methyl-3-nitropyridin-4-amine → 2-Methylpyridine-3,4-diamine

HRID 1463839Notes

Reaction equation

HRID 1463839 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[N+:9]([O-])=O>CO.[Ni]>[NH2:9][C:3]1[C:4]([CH3:8])=[N:5][CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 130403982-Methyl-3-nitropyridin-4-amine

Product 1

HCID 190886662-Methylpyridine-3,4-diamineYield 90.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-Amino-3-nitro-2-picoline (5.5 g, 0.036 mole) was hydrogenated in methanol (250 mL) at 5 psi and 25° for 1.25 hr using Raney Nickel as catalyst. The catalyst was filtered, the filtrate stripped in vacuo and the residue triturated with cyclohexane to give a solid. The solid was filtered and air dried to give 4.0 g (88%) of the title compound, m. pt. 170-171°.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe residue triturated with cyclohexane
  3. customto give a solid
  4. filtrationThe solid was filtered
  5. customair dried

Sources & evidence

ORD record
ord-f4d4aecc49c34b3ca50560641c12138d
Source dataset
uspto-grants-1994_04
Patent number
US05302601

Reaction notes

Loading…