2-Amino-4-methyl-3-nitropyridine → 4-Methylpyridine-2,3-diamine

HRID 53601

Reaction equation

HRID 53601 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1>[Ni].C(O)C>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 2431662-Amino-4-methyl-3-nitropyridine

Product 1

HCID 3174954-Methylpyridine-2,3-diamineYield 100.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-methyl-3-nitropyridine (919 mg, 6.0 mmol), ethanol (20 mL) and Raney Ni (about 200 mg) was shaken under H2 (30-40 psi) for 1 h, then filtered. The filtrate was evaporated to dryness, giving 740 mg (100%) of the diamine 56, mp 114°-5° C. 1H NMR (DMSO-d6), 1.997 (s, 3H), 4.359 (s, 2H), 5.250 (s, 2H), 6.264 (d, 1H, J=3), 7.173 (d, 1H, J=3).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-972228a99c6b4092b37618fa57402f8d
Source dataset
uspto-grants-1997_04
Patent number
US05620978

Linked notes

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