N,N-dimethyl-5-nitropyridin-2-amine → N2,N2-dimethylpyridine-2,5-diamine

HRID 1471023Notes

Reaction equation

HRID 1471023 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][N:4]=1.[H][H]>[Ni].O1CCCC1>[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 75707N,N-dimethyl-5-nitropyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 78642N2,N2-dimethylpyridine-2,5-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 175A (5.27 g, 31.5 mmol) and Raney Nickel (5.27 g, 90 mmol) in tetrahydrofuran (60 mL) was subjected to an atmosphere (30 psi) of hydrogen gas for 2 hours at ambient temperature. Mixture was filtered and concentrated to afford 4.3 g (100%) of the title compound. MS (ESI) m/z 138 (M+H)+.

Workup

  1. filtrationMixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-77a2d698eb374698bbec1149ca1b206f
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

Loading…