Electric Literature of 22223-49-0, A common heterocyclic compound, 22223-49-0, name is Methyl 2-amino-3-methylbenzoate, molecular formula is C9H11NO2, its 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.
A solution of sodium nitrite (1.9 g, 27.6 mmol) in water (5 ml) was added dropwise to an ice-cooled solution of methyl 2-amino-3-methyl benzoate (U.S. Pat. No. 4,657,893 preparation II) (4.14 g, 25 mmol) in acetic acid (50 ml). This solution was then added dropwise to a solution of tert-butyl mercaptan (2.26 g, 25 mmol) in ethanol (70 ml) and stirred at room temperature. The pH of the mixture was adjusted to 5.5 using saturated sodium carbonate solution and the mixture poured into brine. This mixture was extracted with ethyl acetate, the combined organic extracts dried (Na2SO4), concentrated under reduced pressure and the residue azeotroped with dichloromethane and heptane. The residue was dissolved in dimethyl sulphoxide (40 ml) and added dropwise to a suspension of potassium tert -butoxide (14.05 g, 126 mmol) in dimethyl sulphoxide (150 ml), and the reaction stirred at room temperature for 2 hours. The reaction was poured carefully into 1N hydrochloric acid, and extracted with ethyl acetate. The combined organic extracts were washed with 1N hydrochloric acid, dried (Na2SO4) and evaporated under reduced pressure. The product was slurried with isopropanol, sufficient dichloromethane added for complete dissolution, and the solution allowed to evaporate. The resulting solid was filtered off, washed with isopropanol to afford the title compound as an off-white solid. Microanalysis found: C, 59.26; H, 3.73; N, 17.28. C8H6N2O2 requires C, 59.31; H, 3.51; N, 17.42%. aa0-5aa Mpt. 230-233 C.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; Barber, Christopher Gordon; Bunnage, Mark Edward; Harvey, John Wilson; Mathias, John Paul; US2005/20611; (2005); A1;,
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