Oxygen → Ethyl 3-amino-2-methoxy-6-methylpyridine-4-carboxylate

HRID 1861668Notes

Reaction equation

HRID 1861668 reaction equation
O=O.[CH3:3][O:4][C:5]1[C:10]([N+:11]([O-])=O)=[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[C:7]([CH3:19])[N:6]=1.[H][H]>CCOC(C)=O.[Pd]>[NH2:11][C:10]1[C:5]([O:4][CH3:3])=[N:6][C:7]([CH3:19])=[CH:8][C:9]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 3

HCID 977OxygenHCID 15454109HCID 15454109, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15521894Ethyl 3-amino-2-methoxy-6-methylpyridine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an oxygen free solution of the nitro ester 1-2 from step B (2.5 g, 10.4 mmol) in 50 mL of EtOAc was added 520 mg of 10% Pd on charcoal. Hydrogen gas was added and the reaction mixture was stirred for 17 h. The solution was filtered through a pad of Celite, concentrated and chromatographed (2:3 EtOAc/Hexane) to give the desired amine 9-3 as a white solid.

Workup

  1. filtrationThe solution was filtered through a pad of Celite
  2. concentrationconcentrated
  3. customchromatographed (2:3 EtOAc/Hexane)

Sources & evidence

ORD record
ord-a8a84936ff2d43f190d5bcc15e1b6d80
Source dataset
uspto-grants-2003_03
Patent number
US06534510B2

Reaction notes

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