Sodium Hydroxide → 6-Iodo-4-methylpyridin-3-amine
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[I:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.[OH-].[Na+]>Cl.C(OCC)C.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[I:1][C:2]1[N:3]=[CH:4][C:5]([NH2:9])=[C:6]([CH3:8])[CH:7]=1[I:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.[OH-].[Na+]>Cl.C(OCC)C.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[I:1][C:2]1[N:3]=[CH:4][C:5]([NH2:9])=[C:6]([CH3:8])[CH:7]=1
To a solution of 1.76 g of 2-iodo-4-methyl-5-nitropyridine in 7.0 mL of concentrated hydrochloric acid and 7.0 mL of diethyl ether was added 6.32 g of tin chloride (II) at room temperature, and stirred at 100° C. for 4 hours. After cooling the solution to room temperature, 5N sodium hydroxide aqueous solution was added to make the solution alkaline. Then the solution was diluted with dichloromethane and the insoluble substances were filtered off through Celite. The organic layer of the filtrate was dried over anhydrous magnesium sulfate, and the solvent was evaporated, to afford 897 mg of the title compound as orange-brown crystals.
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