Ethyl 2-(3-nitropyridin-2-yl)oxyacetate → Ethyl [(3-amino-2-pyridinyl)oxy]acetate

HRID 1862332Notes

Reaction equation

HRID 1862332 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:5])[CH3:2]>[Pd].C(OCC)(=O)C>[NH2:14][C:13]1[C:8]([O:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 4425975Ethyl 2-(3-nitropyridin-2-yl)oxyacetate

Product 1

HCID 18619191Ethyl [(3-amino-2-pyridinyl)oxy]acetateYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 48.3 g of 2-(ethoxycarbonyl)methoxy-3-nitropyridine, 7.8 g of 10% palladium/carbon and 540 ml of ethyl acetate was stirred for 3 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 37.1 g of 3-amino-2-(ethoxycarbonyl)methoxypyridine. 1H-NMR(CDCl3/300 MHz) δ(ppm): 1.27 (t, 3H, J=7.1 Hz), 3.8-3.9 (b, 2H), 4.24 (q, 2H, J=7.1 Hz), 4.93 (s, 2H), 6.7-6.8 (m, 1H), 6.8-7.0 (m, 1H), 7.4-7.6(m, 1H)

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-67d09618b4604872b32e5d960810156f
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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