New downstream synthetic route of 89793-09-9

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89793-09-9, 2-Chloro-4,6-dimethyl-3-nitropyridine, and friends who are interested can also refer to it.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 89793-09-9, name is 2-Chloro-4,6-dimethyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. 89793-09-9

Step 1, 3-{4-[(4,6-Dimethyl-3-nitro-2-pyridinyl)amino]phenyl}propanoic acid To a solution of 2-chloro-4,6-dimethyl-3-nitropyridine (17.9 g, 96 mmol) and methyl 3-(4-aminophenyl)propanoate (19 g, 96 nmol) in DMSO (100 mL) was added N,N-diisopropylethylamine (26 g, 200 mmol), and the reaction mixture was heated at 140 C. overnight. The reaction mixture was partitioned between water (400 mL) and ethyl acetate/toluene (v/v, 2:1, 300 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate/toluene (v/v, 2:1, 200 mL). The combined organic extracts were washed with brine (200 mL), dried (Na2SO4), and concentrated. To a solution of residual oil in methanol (100 mL) was added 2 N aqueous NaOH (150 mL, 300 mmol) and the resulting mixture was stirred at room temperature for 2 h. The volatile component was removed under reduced pressure and the residue was washed with ethyl acetate (200 mL). The aqueous phase was acidified with 2N hydrochloric acid (200 mL, 400 mmol) and extracted with ethyl acetate (3*200 mL). The extracts were washed with brine (200 mL), dried (Na2SO4), and concentrated to give 23.2 g (77%) of the title compound as pale brown solids. 1H-NMR (CDCl3) delta: 9.57 (1H, s), 7.56 (2H, d, J=8.4 Hz), 7.19 (2H, d, J=8.4 Hz), 6.52 (1H, s), 2.95 (2H, t, J=7.5 Hz), 2.66 (2H, t, J=7.5 Hz), 2.55 (3H, s), 2.43 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89793-09-9, 2-Chloro-4,6-dimethyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Audoly, Laurent; Okumura, Takako; Shimojo, Masato; US2002/77329; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem