Research on new synthetic routes about 1-Methylpyrazole

According to the analysis of related databases, 930-36-9, the application of this compound in the production field has become more and more popular.

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. 930-36-9, name is 1-Methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H6N2

A solution of N-methylpyrazole (5.12 g, 62.4 mmol) in THF (100 mL) was cooled to -78 C. and 2.5 M n-butyllithium in hexane (27.5 mL, 68.8 mmol) was added. After stirring for 30 minutes at the same temperature, 0.5 M zinc chloride in THF (107 mL, 53.5 mmol) and 1 M zinc chloride in diethyl ether (15.3 mL, 15.2 mmol) were added. The mixture was allowed to warm to room temperature and 2-iodo-4-nitroanisole (17.4 g, 62.4 mmol) followed by tetrakis(triphenylphosphine)palladium (3.6 g, 3.1 mmol) were added. After stirring at 60 C. for 20 hours, the black solution was concentrated on a rotary evaporator, and extracted with ethyl acetate and brine. Combined organic layers were dried over magnesium sulfate, filtered, and partly concentrated until a solid started to precipitate. Hexane was added, precipitate was filtered off, and washed with a cold 3:1 mixture of hexane/ethyl acetate to give 5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole (8.6 g, 36.9 mmol, 59%) as a tan solid. LCMS m/z (%/o)=234 (M+H, 100). 1H NMR (400 MHz, CDCl3) delta: 8.34 (dd, J=2.8, 9.2 Hz, 1H), 8.19 (d, J=2.8 Hz, 1H), 7.56 ( d, J=2.0 Hz, 1H), 7.08 (d, J=9.2 Hz, 1H), 6.31 (d, J=1.6 Hz, 1H), 3.96 (s, 3H), 3.74 (s, 3H).

According to the analysis of related databases, 930-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teegarden, Bradley; Xiong, Yifeng; Strah-Pleynet, Sonja; Jayakumar, Honnappa; Dosa, Peter I.; Feichtinger, Konrad; Casper, Martin; Lehmann, Juerg; Jones, Robert M.; Unett, David J.; Karoline Choi, Jin Sun; US2007/207994; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics