Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., name: (2,4-Dimethoxyphenyl)methanamine
1-(2,4-Dimethoxyphenyl)methanamine (20.3 mL, 135 mmol) was added to asolution of C4 (10.3 g, 90.2 mmol) in methanol (200 mL), and the reaction mixture was stirred for 1 hour at room temperature. It was then cooled to -78 C; lithium borohydride solution (2 M in tetrahydrofuran, 45.1 mL, 90.2 mmol) was added drop-wise, and stirring was continued at -78 C for 2 hours. After slowly warming to room temperature overnight, the reaction mixture was quenched via careful addition of saturated aqueous sodium bicarbonate solution. Ethyl acetate (250 mL) and sufficient water to solubilize the precipitate were added, and the aqueous layer was extracted with ethyl acetate; the combined organic layers were dried over magnesium sulfate, filtered, and concentratedin vacuo. Silica gel chromatography (Gradient: 0% to 5% methanol in dichloromethane)provided the product as a colorless oil (10.4 g). Similar purification of mixed fractionsafforded additional product (3.7 g). Combined yield: 14.1 g, 53.1 mmol, 59%. H NMR(400 MHz, CDCI3) 7.13 (d, J=8.0 Hz, 1H), 6.42-6.47 (m, 2H), 3.99 (ddd, J=11.6, 4.6,1.5 Hz, 1H), 3.82 (5, 3H), 3.80 (5, 3H), 3.76 (5, 2H), 3.36-3.45 (m, 2H), 2.63-2.73 (m,1H), 1.85-1.92 (m, 1H), 1.78-1.85 (m, 1H), 1.38 (dddd, J=13, 12, 11,4.7 Hz, 1H), 1.20 (d, J=6.2 Hz, 3H), 1.10(ddd, J=11, 11, 11 Hz, 1H).
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; PFIZER INC.; BRODNEY, Michael Aaron; CHAPPIE, Thomas Allen; CHEN, Jinshan Michael; COE, Jotham Wadsworth; COFFMAN, Karen Jean; GALATSIS, Paul; GARNSEY, Michelle Renee; HELAL, Christopher John; HENDERSON, Jaclyn Louise; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G.; MARTINEZ-ALSINA, Luis Angel; PETTERSSON, Martin Youngjin; REESE, Matthew Richard; ROSE, Colin Richard; STEPAN, Antonia Friederike; VERHOEST, Patrick Robert; WAGER, Travis T.; WARMUS, Joseph Scott; ZHANG, Yuan; (193 pag.)WO2018/163066; (2018); A1;,
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