N,N-dimethyl-6-nitropyridin-3-amine → N5,N5-Dimethylpyridine-2,5-diamine

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Reaction Steps

The N,N-dimethyl-6-nitropyridine-3-amine obtained above is taken up in 25 mL of ethanol. After addition of 4.8 g of stannous chloride, the reaction mixture is refluxed for 30 minutes and then concentrated to dryness. The residue is chromatographed on a column of silica, eluting with a 90/10 mixture of dichloromethane and ammoniacal methanol. The fractions containing the expected product are combined and concentrated to give 750 mg of 5-dimethylaminopyridine-2-amine in the form of a pasty yellow solid.

Provenance & Evidence