2-{1-(Methoxycarbonyl)ethoxy}-3-nitropyridine → 3-Amino-2-{1-(methoxycarbonyl)ethoxy}pyridine

HRID 2214400Notes

Reaction equation

HRID 2214400 reaction equation
[CH3:1][O:2][C:3]([CH:5]([O:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:6])=[O:4]>[Pt]=O.C(O)C>[NH2:14][C:13]1[C:8]([O:7][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 219335712-{1-(Methoxycarbonyl)ethoxy}-3-nitropyridine

Product 1

HCID 219335303-Amino-2-{1-(methoxycarbonyl)ethoxy}pyridineYield 78.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.7 g of 2-{1-(methoxycarbonyl)ethoxy}-3-nitropyridine, 102 mg of platinum oxide, and 7.5 ml of ethanol was stirred at room temperature under an atmosphere of hydrogen gas for 3.5 hours. The gas in the atmosphere on the reaction system was replaced with nitrogen gas, and the reaction mixture was filtered through Celite. The filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 1.16 g of 3-amino-2-{1-(methoxycarbonyl)ethoxy}pyridine.

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-80d92fbbd3924648a7dd7f51f6fc9111
Source dataset
uspto-grants-2006_09
Patent number
US07109148B2

Reaction notes

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