2-氨基-5-氯苯甲酸合成路线 （共 147 条）
反应条件
1.1: sodium nitrite; hydrogenchloride / water / 1 h / 0 °C
1.2: 0 - 90 °C
2.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C
View Scheme
参考文献
Zhou, Ping-Xin; Luo, Jian-Yi; Zhao, Lian-Biao; Ye, Yu-Ying; Liang, Yong-Min
Chemical Communications, 2013 , vol. 49, # 31 p. 3254 - 3256
反应条件
1.1: tetrahydrofuran / 2 h / 70 °C
2.1: triethylamine / ethanol / 0.17 h
2.2: 2 h / |Reflux
3.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / |Inert atmosphere
View Scheme
参考文献
Acker, Timothy M.; Khatri, Alpa; Vance, Katie M.; Slabber, Cathryn; Bacsa, John; Snyder, James P.; Traynelis, Stephen F.; Liotta, Dennis C.
Journal of Medicinal Chemistry, 2013 , vol. 56, # 16 p. 6434 - 6456
反应条件
1: 67 percent / dioxane / 12 h / 20 °C
2: 82 percent / conc. H2SO4; KNO3 / 24 h / 20 °C
3: 82 percent / NaOH / H2O / 3 h / Heating
4: SOCl2 / 3 h / Heating
5: 172 mg / 12 h / 20 °C
View Scheme
参考文献
Zhou, Zhang-Lin; Kher, Sunil M.; Cai, Sui Xiong; Whittemore, Edward R.; Espitia, Stephen A.; Hawkinson, Jon E.; Tran, Minhtam; Woodward, Richard M.; Weber, Eckard; Keana, John F. W.
Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 8 p. 1769 - 1780
反应条件
1: 88 percent / NaN3; AcOH / 19 h / 0 - 20 °C
2: 83 percent / N,N-diisopropylethylamine; [(benzotriazol-1-yloxy)tripyrrolidinophosphonium]*PF6 / CH2Cl2 / 36 h
3: 94 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 °C
View Scheme
参考文献
Howard, Nigel; Abell, Chris; Blakemore, Wendy; Chessari, Gianni; Congreve, Miles; Howard, Steven; Jhoti, Harren; Murray, Christopher W.; Seavers, Lisa C. A.; Van Montfort, Rob L. M.
Journal of Medicinal Chemistry, 2006 , vol. 49, # 4 p. 1346 - 1355
反应条件
(i) aq. HCl, NaNO2, (ii) Na2S, sulfur, NaOH; Multistep reaction;
参考文献
Berryman; Edmunds; Bunker; Haleen; Bryant; Welch; Doherty
Bioorganic and Medicinal Chemistry, 1998 , vol. 6, # 9 p. 1447 - 1456
反应条件
1: With 4-(N,N-dimethlyamino)pyridine; 1-hydroxybenzotriazole-6-sulfonamidomethyl polystyrene resin; diisopropyl-carbodiimide in dichloromethane; N,N-dimethyl-formamide
2 h;
2: With hydroxylamine in tetrahydrofuran; methanol
4 h;
参考文献
Lee, Jean; Chubb, Anthony J.; Moman, Edelmiro; McLoughlin, Brian M.; Sharkey, Caroline T.; Kelly, John G.; Nolan, Kevin B.; Devocelle, Marc; Fitzgerald, Desmond J.
Organic and Biomolecular Chemistry, 2005 , vol. 3, # 20 p. 3678 - 3685
反应条件
1: 1.) conc. HCl, NaNO2, 2.) NaN3, NaOAc / 1.) water, <5 deg C
2: SOCl2 / 2 h / Heating
3: pyridine / 0.5 h / Ambient temperature
View Scheme
参考文献
Ardakani, Manouchehr Azadi; Smalley, Robert K.; Smith, Richard H.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983 , # 10 p. 2501 - 2506
反应条件
1: 1.) conc. HCl, NaNO2, 2.) NaN3, NaOAc / 1.) water, <5 deg C
2: SOCl2 / 2 h / Heating
3: pyridine / 0.5 h / Ambient temperature
4: 71 percent / SOCl2 / Heating
View Scheme
参考文献
Ardakani, Manouchehr Azadi; Smalley, Robert K.; Smith, Richard H.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983 , # 10 p. 2501 - 2506
反应条件
1: 1.) aq. HCl, NaNO2, 2.) Na2SO3 / 1.) <10 deg C, 30 min, 2.) H2O, RT, 2 h
2: conc. HCl / a) RT, overnight, b) 80 deg C, 6 h
3: 76 percent / pyridine / 2 h / Heating
View Scheme
参考文献
Wyrick, Steven D.; Voorstad, P. Josee; Cocolas, George; Hall, Iris H.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 6 p. 768 - 772
反应条件
1: 1.) aq. HCl, NaNO2, 2.) Na2SO3 / 1.) <10 deg C, 30 min, 2.) H2O, RT, 2 h
2: conc. HCl / a) RT, overnight, b) 80 deg C, 6 h
3: 76 percent / pyridine / 2 h / Heating
4: 1.) KOH / 1.) C2H5OH, 2.) C2H5OH, reflux, 6 h
5: 14 percent / KOH / ethanol / 4 h / Heating
View Scheme
参考文献
Wyrick, Steven D.; Voorstad, P. Josee; Cocolas, George; Hall, Iris H.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 6 p. 768 - 772
