2-Ethoxy-5-nitropyridine → 6-Ethoxypyridin-3-amine

HRID 2184752Notes

Reaction equation

HRID 2184752 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][N:5]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][N:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 2958642-Ethoxy-5-nitropyridine

Product 1

HCID 30403016-Ethoxypyridin-3-amineYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-ethoxy-5-nitropyridine (3.60 g) and 10% Pd/C (360 mg) in ethanol (40 mL) was placed in a Paar bottle and shaken under hydrogen (50 PSI) for 16 h. The mixture was filtered through Celite using dichloromethane and concentrated to give 2.892 g of 2-ethoxy-5-aminopyridine as a gold solid.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7ab8a3208cbc4bbcbf34d255cbac2967
Source dataset
uspto-grants-2002_06
Patent number
US06399604B1

Reaction notes

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