5-氯-3,4-二氢喹啉-2(1H)-酮合成路线 （共 11 条）
反应条件
sodium nitrite; Copper(I)chloride in hydrogenchloride; ethanol; chloroform; water
参考文献
Otsuka Pharmaceutical Co., Ltd.
Patent: US4416884 A1, 1983 ;
反应条件
hydrogenchloride; acetic acid in water
T=90°C; 1 h;
参考文献
MERCK SHARP and DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.
Patent: WO2012/148808 A1, 2012 ;
Location in patent: Page/Page column 138 ;
WO 2012/148808 A1
反应条件
2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in dimethyl sulfoxide
T=0 - 120°C; 16 h;
参考文献
MERCK SHARP and DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.
Patent: WO2012/148808 A1, 2012 ;
Location in patent: Page/Page column 131 ;
WO 2012/148808 A1
反应条件
1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C
1.2: 0.75 h / 0 °C
2.1: ethanol; SnCl2·2H2O / 0.5 h / 0 - 70 °C
3.1: hydrogenchloride; acetic acid / water / 1 h / 90 °C
View Scheme
参考文献
MERCK SHARP and DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.
Patent: WO2012/148808 A1, 2012 ;
WO 2012/148808 A1
反应条件
1: potassium tert-butylate; copper(l) chloride; N-methoxyamine hydrochloride / N,N-dimethyl-formamide / 1 h / 15 - 20 °C
2: hydrogenchloride; potassium iodide; sodium nitrite / water / 20 °C / Cooling with ice
3: ethanol; SnCl2·2H2O / 0.5 h / 0 - 70 °C
4: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / dimethyl sulfoxide / 16 h / 0 - 120 °C
View Scheme
参考文献
MERCK SHARP and DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.
Patent: WO2012/148808 A1, 2012 ;
WO 2012/148808 A1
反应条件
1.1: dibenzoyl peroxide; N-bromosuccinmide / 4 h / 0 °C / Reflux
2.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C
2.2: 0.75 h / 0 °C
3.1: ethanol; SnCl2·2H2O / 0.5 h / 0 - 70 °C
4.1: hydrogenchloride; acetic acid / water / 1 h / 90 °C
View Scheme
参考文献
MERCK SHARP and DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.
Patent: WO2012/148808 A1, 2012 ;
WO 2012/148808 A1
反应条件
1: hydrogenchloride; potassium iodide; sodium nitrite / water / 20 °C / Cooling with ice
2: ethanol; SnCl2·2H2O / 0.5 h / 0 - 70 °C
3: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / dimethyl sulfoxide / 16 h / 0 - 120 °C
View Scheme
参考文献
MERCK SHARP and DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.
Patent: WO2012/148808 A1, 2012 ;
WO 2012/148808 A1
反应条件
1: ethanol; SnCl2·2H2O / 0.5 h / 0 - 70 °C
2: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / dimethyl sulfoxide / 16 h / 0 - 120 °C
View Scheme
参考文献
MERCK SHARP and DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.
Patent: WO2012/148808 A1, 2012 ;
WO 2012/148808 A1
反应条件
1: ethanol; SnCl2·2H2O / 0.5 h / 0 - 70 °C
2: hydrogenchloride; acetic acid / water / 1 h / 90 °C
View Scheme
参考文献
MERCK SHARP and DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.
Patent: WO2012/148808 A1, 2012 ;
WO 2012/148808 A1
反应条件
hydrogenchloride; copper(l) chloride; sodium nitrite
1.) H2O, RT; 1 h, 2.) 50 to 60 deg C, 1 h,; Yield given. Multistep reaction;
参考文献
Ishikawa; Tabusa; Miyamoto; Kano; Ueda; Tamaoka; Nakagawa
Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 8 p. 2103 - 2108
