5-Chloro-2-methoxy-3-nitropyridine → 5-Chloro-2-methoxypyridin-3-amine

HRID 573982Notes

Reaction equation

HRID 573982 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1>[Pt].C(OCC)(=O)C.[Br-].[Zn+2].[Br-]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 1

HCID 263702185-Chloro-2-methoxy-3-nitropyridine

Product 1

HCID 451221815-Chloro-2-methoxypyridin-3-amineYield 100%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Zinc bromide (0.27 g, 1.2 mmol) and 10% platinum on carbon (0.58 g, 2.97 mmol) were added to a solution of 5-chloro-2-methoxy-3-nitropyridine (Preparation 6a, 1.13 g, 5.99 mmol) in ethyl acetate (20 mL) and the resulting mixture was hydrogenated in a Parr apparatus at 10 psi for 2 hours. The mixture was then filtered through diatomaceous earth (Celite®) and the filter cake was washed with ethyl acetate. The combined filtrate and washings were concentrated to give the title compound (0.95 g, 100%) as an oil which was used in the next synthetic step without further purification.

Workup

  1. filtrationThe mixture was then filtered through diatomaceous earth (Celite®)
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationThe combined filtrate and washings were concentrated

Sources & evidence

ORD record
ord-9a2fd9244b1a4588b7db39fc72aff918
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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