2-Methoxy-3-nitropyridine → 3-Amino-2-methoxypyridine

HRID 70521Notes

Reaction equation

HRID 70521 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[CH:5][N:4]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 2532192-Methoxy-3-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 27374883-Amino-2-methoxypyridineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% palladium-activated carbon (2.5 g) was added to a solution of commercially available 2-methoxy-3-nitropyridine (50.5 g) in methanol (500 mL), and the mixture was stirred for four hours in a hydrogen atmosphere. The reaction solution was filtered through celite, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give 2-methoxypyridin-3-amine as a yellow powder (37.2 g, 92%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-1416a950087e4723ba3ed4261c7815ab
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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