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

HRID 450178

Reaction equation

HRID 450178 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>CO.[Pd]>[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 75707N,N-dimethyl-5-nitropyridin-2-amine

Product 1

HCID 78642N2,N2-dimethylpyridine-2,5-diamineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.312 g (1.87 mmol) of the above nitro compound and 0.205 g of 10% Pd/C in methanol (40 mL) was stirred under hydrogen (25 in/Hg) for 5 hrs. The reaction mixture was filtered through celite, and the solvent was concentrated, to give 0.236 g (92% yield) of N2,N2-dimethyl-2,5-pyridinediamine: 1H NMR (CDCl3) δ7.78 (d, J=2.9 Hz, 1H), 6.98 (dd, J=8.8, 2.9 Hz, 1H), 6.45 (dd, J=8.8, 0.5 Hz, 1H), 2.99 (s, 6H); LCMS (APCI+) m/z: 138 (MH+, 100%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-15192473680a4141831ad8eeab478da1
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Linked notes

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