Methyl 2-(3-nitropyridin-2-yloxy)acetate → 3-Amino-2-(methoxycarbonyl)methoxypyridine

HRID 493951Notes

Reaction equation

HRID 493951 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:4]>[Pt]=O.C(O)C>[NH2:13][C:12]1[C:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 12115511Methyl 2-(3-nitropyridin-2-yloxy)acetate

Product 1

HCID 121155123-Amino-2-(methoxycarbonyl)methoxypyridineYield 85.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.3 g of 2-(methoxycarbonyl)methoxy-3-nitropyridine, 20 mg of platinum oxide, and 1.4 ml of ethanol was stirred at room temperature under an atmosphere of hydrogen gas for 3 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 0.22 g of 3-amino-2-(methoxycarbonyl)methoxypyridine.

Workup

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

Sources & evidence

ORD record
ord-1fc554709c954950a23efb12e2d8eae9
Source dataset
uspto-grants-2009_05
Patent number
US07538072B2

Reaction notes

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