Related Products of 159847-81-1,Some common heterocyclic compound, 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, molecular formula is C9H8N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a solution of methyl 2-amino-5-cyanobenzoate (5.68 mmol) in DCM (lOmL) was added triethyamine (8.52 mmol) followed by methyl 3-chloro-3-oxopropionate (7.38 mmol). The resulting reaction mixture was stirred at ambient temperature overnight. The reaction mixture was partitioned between EtOAc and IM HCI and the layers then separated. The organic layer washed sequentially with saturated aqueous NaHCO, followed by brine. The organic layer was diied over Na2S04, filtered, and concentrated in vacuo. The resulting residue was carried on without further purification. [00170] The residue from above was treated with 0.5M NaOMe in MeOH (6.83 mmol). The heterogenous mixture was stirred at ambient temperature for 30 min. Diethyl ether was then added to the reaction mixture and the solid was collected via vacuum filtration, washing with ether. The obtained solid was carried on without further purification. [00171] To a flask containing the solid from above cooled to 0 C was added POCK (15 mL). The mixture became warm and bubbled. The resulting reaction mixture was heated to 90C for 3 h. Cooled the dark reaction mixture to ambient temperature and poured it very slowly into stirring saturated aqueous NaHCOj cooled to 0 C. Solid NaHCQs was then added until the solution was basic. The aqueous solution was extracted with EtOAc (3x). The combined organic layers were dried over a2S04, filtered, and concentrated in vacuo. The obtained residue was purified via flash column chromatography, eluting with 9: l/hexanes:EtOAc, to yield the intermediate 13 (29% over 3 steps). MS ESI (m/z) 281 (M+ J ); ;H NMR (300 MHz, CDCi3) 5 8.63 (d, 1 H, J=l .8 Hz), 8.16 (d, 1H, ./ 8 · Hz), 8.00 (dd, lH, Hz), 4.08 (s, 3H); i C NMR (CDC , 75MHz) 5 163.4, 148.9, 148.1 , 141 .8, 1 33.3, 130.8, 130.6, 128.8, 124.3, 1 17.7, 1 12.8, 54.1.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-5-cyanobenzoate, its application will become more common.