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

HRID 1862261Notes

Reaction equation

HRID 1862261 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 for 3.5 hours at room temperature under hydrogen atmosphere. The reaction system was purged with nitrogen, then, the reaction solution was filtrated through Celite, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to obtain 1.16 g of 3-amino-2-{1-(methoxycarbonyl)ethoxy}pyridine.

Workup

  1. customThe reaction system was purged with nitrogen
  2. filtrationthe reaction solution was filtrated through Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-edfbf264ea944565820c9af1c7946d5e
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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