5-氯-2-羟基苯甲酸甲酯合成路线 （共 50 条）
反应条件
1: 86 percent / HNO3, conc. H2SO4 / 1 h / 0 - 5 °C 2: 79 percent / 0.78N aq. NH4Cl, Fe / toluene / 1 h / 85 - 90 °C 3: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 4: K2CO3 / dimethylformamide / 2 h / 70 °C 5: 82.2 percent / K2CO3 / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h 6: 81.5 percent / 5percent NaOH / ethanol / 3 h / Heating View Scheme
参考文献
Kawakita; Kuroita; Yasumoto; Sano; Inaba; Fukuda; Tahara
Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 3 p. 624 - 630
反应条件
1: 86 percent / HNO3, conc. H2SO4 / 1 h / 0 - 5 °C 2: 79 percent / 0.78N aq. NH4Cl, Fe / toluene / 1 h / 85 - 90 °C 3: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 4: K2CO3 / dimethylformamide / 2 h / 70 °C 5: 82.2 percent / K2CO3 / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h 6: 81.5 percent / 5percent NaOH / ethanol / 3 h / Heating 7: SOCl2, DMF / 1,2-dichloro-ethane / 2 h / 60 °C 8: CHCl3 / 1 h / Ambient temperature View Scheme
参考文献
Kawakita; Kuroita; Yasumoto; Sano; Inaba; Fukuda; Tahara
Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 3 p. 624 - 630
反应条件
1: 86 percent / HNO3, conc. H2SO4 / 1 h / 0 - 5 °C 2: 79 percent / 0.78N aq. NH4Cl, Fe / toluene / 1 h / 85 - 90 °C 3: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 4: K2CO3 / dimethylformamide / 2 h / 70 °C View Scheme
参考文献
Kawakita; Kuroita; Yasumoto; Sano; Inaba; Fukuda; Tahara
Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 3 p. 624 - 630
反应条件
1: NH2OH*HCl, aq. NaOH 2: carbonyldiimidazole / tetrahydrofuran / Heating 3: POCl3, Et3N / Heating View Scheme
参考文献
Yevich, Joseph P.; New, James S.; Smith, David W.; Lobeck, Walter G.; Catt, John D.; et al.
Journal of Medicinal Chemistry, 1986 , vol. 29, # 3 p. 359 - 369
反应条件
1: 86 percent / HNO3, conc. H2SO4 / 1 h / 0 - 5 °C 2: 79 percent / 0.78N aq. NH4Cl, Fe / toluene / 1 h / 85 - 90 °C 3: aq. NaHCO3 / CHCl3 / 2 h / 0 - 10 °C 4: K2CO3 / dimethylformamide / 2 h / 70 °C 5: 82.2 percent / K2CO3 / dimethylformamide / a) RT, 3 h, b) 40-45 deg C, 1 h 6: 81.5 percent / 5percent NaOH / ethanol / 3 h / Heating 7: SOCl2, DMF / 1,2-dichloro-ethane / 2 h / 60 °C View Scheme
参考文献
Kawakita; Kuroita; Yasumoto; Sano; Inaba; Fukuda; Tahara
Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 3 p. 624 - 630
反应条件
1: 29 percent / K2CO3 / acetone / Heating 2: 81.7 percent / N-methylpyrrolidinone / 7 h / Heating 3: 90percent aq. HCOOH / 3 h / Heating 4: NaOH / H2O / 3 h / Heating 5: SOCl2 / 3 h / Heating 6: toluene / Heating View Scheme
参考文献
Robertson, David W.; Lacefield, William B.; Bloomquist, William; Pfeifer, William; Simon, Richard L.; Cohen, Marlene L.
Journal of Medicinal Chemistry, 1992 , vol. 35, # 2 p. 310 - 319
反应条件
ethanol; hydroxylamine
参考文献
Yevich, Joseph P.; New, James S.; Smith, David W.; Lobeck, Walter G.; Catt, John D.; et al.
Journal of Medicinal Chemistry, 1986 , vol. 29, # 3 p. 359 - 369
反应条件
potassium carbonate in acetonitrile
参考文献
Cell Therapeutics, Inc.
Patent: US2003/153570 A1, 2003 ;
反应条件
1.1: potassium carbonate / acetone / Reflux
2.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C
3.1: sodium tetrahydroborate; methanol / 4 h / 0 - 20 °C
4.1: diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0 - 20 °C
5.1: triphenylphosphine; water / tetrahydrofuran / 50 °C
5.2: 0.08 h / 20 °C
6.1: sodium hydrogencarbonate; sodium hydroxide / water / pH 9
View Scheme
参考文献
PFIZER INC.; AM ENDE, Christopher William; JOHNSON, Douglas Scott; O'DONNELL, Christopher John; PETTERSSON, Martin Youngjin; SUBRAMANYAM, Chakrapani
Patent: WO2011/48525 A1, 2011 ;
WO 2011/048525 A1
参考文献
Benedini, Francesca; Bertolini, Giorgio; Cereda, Roberta; Dona, Giancarlo; Gromo, Gianni; et al.
Journal of Medicinal Chemistry, 1995 , vol. 38, # 1 p. 130 - 136
