Application of 1089330-68-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1089330-68-6, name is 5-Methyl-3-nitropicolinonitrile, molecular formula is C7H5N3O2, molecular weight is 163.13, as common compound, the synthetic route is as follows.
[00261] To acetic acid (300 ml_) in a 3-neck 2 liter round bottom flask equipped with mechanical stirrer and a thermometer was added Fe powder (99.6 g, 1.78 mol) with stirring at 60 0C. 2-Cyano-5-methyl-3- nitropyridine (97 g, 0.59 mol) was dissolved in acetic acid (400 ml_) with gentle warming and added to the above reaction mixture drop wise with efficient stirring so that the reaction temperature kept below 80 “C over 3.5 hours. The reaction mixture was further stirred for an addition 30 min, cooled, diluted with EtOAc (750 ml_), filtered through celite and washed with EtOAc (1 x 500 ml_, 3 x 250 ml_). Combined EtOAc layers were evaporated to dryness to obtain dark brown solid which was neutralized with saturated NaHCO3 solution (850 ml_), after addition of water (250 ml_) to obtain homogeneous, this aqueous layer was extracted with EtOAc (1 x 750 mL, 2 x 500 mL). Combined EtOAc layers were filtered through small pad of silica gel (sand-SiO2-sand in sintered funnel), dried (Na2SO4) and evaporated to obtain 3-amino-2-cyano-5-methylpyridine (60 g) as yellow solid in 76% yield including -10% corresponding amide.[00262] To the crude 3-amino-2-cyano-5-methylpyridine (containing~10% carboxamide) (49 g) was added EtOAc (441 mL, 9: 1 volume ratio to aniline), the resulting suspension was heated to reflux to form a clean solution. After cooling to room temperature, the resulting crystal was collected by filtration, washed with small amount of cold EtOAc (44 mL (1/10 the initial volume) X 2), and dried in vacuo to afford the pure 3-amino-2-cyano-5- methylpyridine (35 g) as pale yellow needles. The mother liquor was concentrated under reduced pressure, the resulting yellow solid was added EtOAc (136 mL) and repeated the above process to afford another 4 g of pure 3-amino-2-cyano-5-methylpyridine; total recovery yield 79.5%. 1H NMR (400 MHz, CDCI3) delta 7.89 (1 H, s), 6.90 (1 H, s), 4.39 (2H, br), 2.30 (3H, s). MS (ES) M+H expect 134.0, found 134.0.
The chemical industry reduces the impact on the environment during synthesis 1089330-68-6, I believe this compound will play a more active role in future production and life.
Reference:
Patent; CHEMOCENTRYX, INC.; WO2009/9740; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem