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

HRID 1862300Notes

Reaction equation

HRID 1862300 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]>[Pd].C(OCC)(=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 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 55.9 g of 2-(methoxycarbonyl)methoxy-3-nitropyridine, 8.64 g of 10% palladium/carbon and 600 ml of ethyl acetate was stirred for 2 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 46.76 g of 3-amino-2-(methoxycarbonyl)methoxypyridine. Intermediate Production Example 8

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-ef265a7c85714a58b1a418e6c6d77a91
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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