2-甲基-3-硝基苯甲酸合成路线 （共 60 条）
反应条件
1: 100 percent / BH3 / tetrahydrofuran 2: 100 percent / SOCl2, pyridine 3: 99 percent / ethanol; H2O 4: 97 percent / H2SO4, HOAc / H2O 5: SOCl2 6: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 7: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 8: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 9: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature View Scheme
参考文献
Gallagher, Gregory; Lavanchy, Patricia G.; Wilson, James W.; Hieble, J. Paul; DeMarinis, Robert M.
Journal of Medicinal Chemistry, 1985 , vol. 28, # 10 p. 1533 - 1536
反应条件
1: 100 percent / BH3 / tetrahydrofuran 2: 100 percent / SOCl2, pyridine 3: 99 percent / ethanol; H2O 4: 97 percent / H2SO4, HOAc / H2O 5: SOCl2 6: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h View Scheme
参考文献
Gallagher, Gregory; Lavanchy, Patricia G.; Wilson, James W.; Hieble, J. Paul; DeMarinis, Robert M.
Journal of Medicinal Chemistry, 1985 , vol. 28, # 10 p. 1533 - 1536
反应条件
1: 1.) KHCO3 / 1.) DMF, 40 deg C, 2.) DMF, RT, 12 h 2: dimethylformamide / 12 h / 120 °C 3: H2 / 10 percent Pd/C / benzene / 12 h / 2844.31 Torr / Ambient temperature 4: 100 percent / DMAP / acetonitrile / 12 h / Ambient temperature 5: 88 percent / DIBAL / diethyl ether; CH2Cl2 / 0.5 h / -78 °C View Scheme
参考文献
Fauq, Abdul H.; Hong, Feng; Cusack, Bernadette; Tyler, Beth M.; Ping-Pang, Yuan; Richelson, Elliott
Tetrahedron Asymmetry, 1998 , vol. 9, # 23 p. 4127 - 4134
反应条件
1: 1.) KHCO3 / 1.) DMF, 40 deg C, 2.) DMF, RT, 12 h 2: dimethylformamide / 12 h / 120 °C 3: H2 / 10 percent Pd/C / benzene / 12 h / 2844.31 Torr / Ambient temperature 4: 100 percent / DMAP / acetonitrile / 12 h / Ambient temperature View Scheme
参考文献
Fauq, Abdul H.; Hong, Feng; Cusack, Bernadette; Tyler, Beth M.; Ping-Pang, Yuan; Richelson, Elliott
Tetrahedron Asymmetry, 1998 , vol. 9, # 23 p. 4127 - 4134
反应条件
1.1: H2 / Pd/C 2.1: NaNO2; H+ 2.2: potassium ethyl xanthogenate; aq. Na2CO3 / pH 8 2.3: 14.66 g / aq. NaOH / 20 h / Heating 3.1: 93 percent / H2SO4 / 48 h / Heating View Scheme
参考文献
Kuehler, Thomas C.; Swanson, Marianne; Christenson, Beritte; Klintenberg, Ann-Charlotte; Lamm, Bo; Faegerhag, Jonas; Gatti, Roberto; Oelwegard-Halvarsson, Maria; Shcherbuchin, Vladimir; Elebring, Thomas; Sjoestroem, Jan-Erik
Journal of Medicinal Chemistry, 2002 , vol. 45, # 19 p. 4282 - 4299
反应条件
1: 1.) KHCO3 / 1.) DMF, 40 deg C, 2.) DMF, RT, 12 h 2: dimethylformamide / 12 h / 120 °C 3: H2 / 10 percent Pd/C / benzene / 12 h / 2844.31 Torr / Ambient temperature 4: 100 percent / DMAP / acetonitrile / 12 h / Ambient temperature 5: 88 percent / DIBAL / diethyl ether; CH2Cl2 / 0.5 h / -78 °C 6: 84 percent / PBr3 / diethyl ether; CH2Cl2 / 0.5 h / 0 °C View Scheme
参考文献
Fauq, Abdul H.; Hong, Feng; Cusack, Bernadette; Tyler, Beth M.; Ping-Pang, Yuan; Richelson, Elliott
Tetrahedron Asymmetry, 1998 , vol. 9, # 23 p. 4127 - 4134
反应条件
1.1: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 °C 1.2: 72 h / 20 °C / |Cooling with ice 2.1: manganese(IV) oxide / chloroform / 5 h / |Reflux View Scheme
参考文献
SUMITOMO CHEMICAL COMPANY, LIMITED; YOSHIMOTO, Yuya; ARIMORI, Sadayuki; MATSUZAKI, Yuichi
Patent: WO2013/162072 A1, 2013 ;
反应条件
1.1: 1,3-dibromo-5,5-dimethyl-hydantoin; sulfuric acid / 5 h / 20 °C 2.1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3.1: ammonium chloride; iron / ethanol; water / 1 h / 90 °C 4.1: potassium acetate / chloroform / 12 h / 20 °C 4.2: 3 h / 65 °C 5.1: hydrogenchloride / water; methanol / 8 h / 60 °C 5.2: pH 8 View Scheme
参考文献
EPIZYME, INC.; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; CHESWORTH, Richard; DUNCAN, Kenneth, William
Patent: WO2012/118812 A2, 2012 ;
WO 2012/118812 A2
反应条件
1: thionyl chloride 2: benzene; pyridine 3: Raney nickel; ethanol / Hydrieren des Reaktionsprodukts an Raney-Nickel in Aethanol View Scheme
参考文献
Sorkin; Kraehenbuehl; Erlenmeyer
Helvetica Chimica Acta, 1948 , vol. 31, p. 65,74
反应条件
Sodium bromate; sodium hydrogensulfite in water; ethyl acetate T=20°C; 40 h;
参考文献
Bayer, Ernst; Hayat, Safdar; Atta-Ur-Rahman; Choudhary, M. Iqbal; Khan, Khalid Mohammed; Shah, Syed Tasadaque Ali; Imran-Ul-Haq; Anwar, M. Usman; Voelter, Wolfgang
Arzneimittel-Forschung/Drug Research, 2005 , vol. 55, # 10 p. 588 - 597
