* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Advanced Synthesis and Catalysis, 1997, vol. 339, # 4, p. 335 - 339
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 494
[3] Organic Letters, 2012, vol. 14, # 21, p. 5618 - 5620
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[ 18368-71-3 ]
[ 33225-74-0 ]
Reference：
[1] Journal of the American Chemical Society, 1954, vol. 76, p. 3167
In DMF (N,N-dimethyl-formamide); at 140℃; for 2.0h;
Method 31; 3-Nitroisonicotinaldehyde 4-Methyl-nitropyridine (1.43g, 10.36mmol) was dissolved in dry DMF (5mL) and dimethylformamide dimethyl acetal (2. 0g, 16. 8mmol) was added. The mixture was heated under nitrogen at 140C for 2 hours and then evaporated under reduced pressure to give (E)- N, dimethyl-2-(3-nitropyridin-4-yl)ethyleneamine as a dark red solid. This was added in one portion at ambient temperature to a stirred solution of sodium periodate (6. 61g, 31mmol) in THF/ 1 1:1 (100mL). After stirring for 2hr at ambient temperature the reaction mixture was filtered and the solid washed with ethyl acetate (100mL). The washings were combined with the filtrate and organic layer separated. The aqueous was extracted with ethyl acetate (2 x lOOmL) and the combined organic layers were washed with saturated aqueous sodium bicarbonate (lOOmL) and brine (lOOmL), dried (MgS04) and evaporated under reduced pressure to give a brown solid which was purified by column chromatography (DCM) to give the title compound. (960mg, 61%). 1HNMR 7. 8 (d, 1H) ; 9. 15 (d, 1H) ; 9. 4 (s, 1H) ; 10. 4 (s, 1H)
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