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]=1

Participants

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.