Pyridine methylamine compound and preparation method thereof
A technology of picolylamine and its compound, which is applied in the field of picolylamine compounds and their preparation, can solve the problems of Raney nickel catalyst use danger, unreachable conditions, limited use range, etc., achieve less environmental hazards, avoid explosions, and handle low cost effect
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[0042]
[0043] Such as figure 1 Shown, the reaction formula of the preparation method of the picolylamine compound of the present invention is:
[0044]
[0045] Specifically include the following steps:
[0046] (1) Weigh the cyanopyridine compound into the three-necked flask, add tetrahydrofuran and sodium borohydride in turn for stirring, then add the prepared tetrahydrofuran solution containing iodine dropwise, react at 20-30°C, after the dropwise addition , continue stirring at 20-30°C;
[0047] (2), after the LC-MS monitoring reaction is completed, concentrate and spin to dry, add methanol to reflux, and spin to dry, then extract, spin to dry, repeat the above operations to obtain picolylamine compounds with a purity of more than 95%, and a yield of 60-90%.
[0048] Wherein, in step (1), the functional group in the cyanopyridine compound is selected from chlorine, bromine, methyl, ethyl, amino or hydrogen.
[0049] In step (1), the time for dropping can be 0.5-...
Embodiment 1
[0061] (1), 24g of 4-cyano-2-bromopyridine was weighed and added into a 1L there-necked flask, followed by adding 300mL tetrahydrofuran and 20g sodium borohydride for stirring, and then adding dropwise the previously prepared iodine-containing tetrahydrofuran solution (66.6 g iodine dissolved in 200mL tetrahydrofuran), react at 20°C, add dropwise for 1h, and continue stirring at 20°C for 16h.
[0062](2), LC-MS monitoring after the reaction is completed, concentrate and spin dry, add 120mL methanol to reflux for 3h, and spin dry, then add 120mL ethyl acetate and 120mL water, separate the layers, and use 200mL ethyl acetate (EA) for the water layer Extract, combine organic layer, spin dry, obtain 16.2g yellow oil, from Figure 2 to Figure 4 It can be seen that the purity is above 95%, and the yield is 66%. The details of the reaction reagents are shown in Table 1.
[0063] Among them, the reaction equation is:
[0064]
[0065] Table 1 The parameters of each reagent
[0...
Embodiment 2
[0068] (1), 25g of 4-cyano-2-chloropyridine was weighed and added to a 1L there-necked flask, followed by adding 300mL tetrahydrofuran and 41g sodium borohydride to stir, and then dropwise added the pre-prepared iodine-containing tetrahydrofuran solution (137.4 g iodine dissolved in 200mL tetrahydrofuran), reacted at 25°C, added dropwise in 1.5h, and continued to stir at 25°C for 16h.
[0069] (2), LC-MS monitoring after the reaction is completed, concentrate and spin dry, add 120mL methanol to reflux for 3h, and spin dry, then add 120mL ethyl acetate and 120mL water, separate the layers, and use 200mL ethyl acetate (EA) for the water layer Extract, combine organic layer, spin dry, obtain 18.3g white solid, from Figure 5 to Figure 7 It can be seen that the purity is above 96%, and the yield is 71%. The details of the reaction reagents are shown in Table 2.
[0070] Among them, the reaction equation is:
[0071]
[0072] Table 2 The parameters of each reagent
[0073] ...
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