5-Chloro-2-methoxy-3-nitropyridine → 5-Chloro-2-methoxypyridin-3-amine
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]=1Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
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
- filtrationThe mixture was then filtered through Celite®
- washthe filter cake was washed with methanol
- 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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