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

HRID 2236154Notes

Reaction equation

HRID 2236154 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]>[Pd].CO>[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 139.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of dimethyl-(5-nitro-pyridin-2-yl)-amine (100 mg, 0.47 mmol) and 10% palladium on carbon (0.05 g) in methanol (5 mL) was shaken under 50 psi hydrogen atmospheres at room temperature for 3 h. The reaction mixture was then filtered through a plug of celite and the filtration pad was washed with ethyl acetate. The organic layers were collected, concentrated, and dried to give N2,N2-dimethyl-pyridine-2,5-diamine (90 mg crude) as a light red oil, which was directly used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered through a plug of celite
  2. washthe filtration pad was washed with ethyl acetate
  3. customThe organic layers were collected
  4. concentrationconcentrated
  5. customdried

Sources & evidence

ORD record
ord-2de6a69ef6384292a4e2aa88471607fa
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

Loading…