4-Methoxy-3-nitropyridine → 3-Amino-4-methoxypyridine

HRID 550833

Reaction equation

HRID 550833 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[N+:9]([O-])=O.C(OCC)(=O)C.CCCCCC>C(O)C.[Pd]>[NH2:9][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 3558324-Methoxy-3-nitropyridineHCID 21226206Ethyl acetate hexane

Product 1

HCID 52003433-Amino-4-methoxypyridineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 4-Methoxy-3-nitropyridine (5.0 g, 32.44 mmole) in ethanol (100 mL) was added 10% palladium on carbon catalyst (200 mg). The resulting mixture was allowed to shake under a hydrogen atmosphere (50 psi) for 6 h. at room temperature. TLC (50% ethyl acetate/hexane) indicated complete consumption of starting material. Filtration through celite to remove the catalyst and concentration gave 3- Amino-4 methoxypyridine (4.0 g, 32.44 mmol, 100% yield) as dark red oil.

Workup

  1. customfor 6 h.
  2. customat room temperature
  3. customconsumption of starting material
  4. filtrationFiltration through celite
  5. customto remove
  6. concentrationthe catalyst and concentration

Sources & evidence

ORD record
ord-e4cd080d4e2c42e1ac5b0bb33c880ad4
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Linked notes

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