Hydrochloric Acid → 2-Chloro-5-iodo-3-methylpyridine
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[Cl:1]Cl.Cl.N[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][N:6]=1.N([O-])=O.[Na+]>O>[Cl:1][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][N:6]=1[Cl:1]Cl.Cl.N[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][N:6]=1.N([O-])=O.[Na+]>O>[Cl:1][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][N:6]=1At −10° C., 21.3 g of chlorine gas were introduced into a suspension of 146 g of 10% strength by weight hydrochloric acid and 23.4 g of 2-amino-3-methyl-5-iodopyridine [J. Org. Chem. (1995), p. 5356]. At about −50° C., a solution of 48.3 g of sodium nitrite in 120 ml of water was subsequently added dropwise. After about 2 hours of stirring at 0° C., the mixture was diluted with 1 l of water and extracted with methyl tert-butyl ether (MtBE). The organic phases were washed with NaHCO3 solution and water and then dried. Distillative removal of the solvent under reduced pressure and silica gel chromatography (cyclohexane/MtBE=1:10) gave 3.6 g of the product in the form of dark crystals.
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