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

HRID 2279078Notes

Reaction equation

HRID 2279078 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 102.6%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Zinc bromide (226 mg, 1 mmol) and platinum on carbon (5%, 491 mg, 2.52 mmol) were added to a solution of 5-chloro-2-methoxy-3-nitropyridine (Preparation 23a, 950 mg, 5.04 mmol) in ethyl acetate (15 mL) and the reaction mixture was stirred at ambient temperature for 5 hours under a hydrogen atmosphere. The mixture was then filtered through Celite® and the filter cake was washed with methanol. The combined filtrate and washings were concentrated to give the title compound (820 mg, 100%) as a white solid.

Workup

  1. filtrationThe mixture was then filtered through Celite®
  2. washthe filter cake was washed with methanol
  3. concentrationThe combined filtrate and washings were concentrated

Sources & evidence

ORD record
ord-c22281cbf1d44ae4b973e6e0045781fd
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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