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[ CAS No. 35478-79-6 ] {[proInfo.proName]}

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Chemical Structure| 35478-79-6
Chemical Structure| 35478-79-6
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Product Details of [ 35478-79-6 ]

CAS No. :35478-79-6 MDL No. :MFCD22395081
Formula : C10H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 189.17 Pubchem ID :-
Synonyms :

Safety of [ 35478-79-6 ]

Signal Word: Class:N/A
Precautionary Statements: UN#:N/A
Hazard Statements: Packing Group:N/A

Application In Synthesis of [ 35478-79-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 35478-79-6 ]

[ 35478-79-6 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 35478-79-6 ]
  • [ 59134-89-3 ]
YieldReaction ConditionsOperation in experiment
63% With trichlorophosphate for 5h; Heating;
With trichlorophosphate In toluene 4-chloro-6,7-methylenedioxyquinoline. 4-chloro-6,7-methylenedioxyquinoline. A reaction mixture containing 18.9 g (0.1 mole) of 4-hydroxy-6,7-methylenedioxyquinoline, 46 g (0.3 mole) of POCl3 and 50 ml of toluene was heated at reflux for 2 hours. The volatile components of the mixture were removed by evaporation and the residue which remained was triturated with excess saturated K2 CO3 solution. The tan solid which remained was further washed with H2 O and dried. The crude product was recrystallized from Skelly C to give the analytical product as crystalline platelets in good yield, mp 130°-132°. Anal. Calcd. for C10 H6 ClNO2: C, 57.85; H, 2.91; N, 6.75; Cl, 17.08. Found: C, 57.79; H, 2.96; H, 6.77; Cl, 17.04.
Reference： [1]Gall-Istok, K.; Sterk, L.; Deak, Gy. [Acta Chimica Hungarica, 1983, vol. 112, # 2, p. 241 - 252]
[2]Ruchelman, Alexander L.; Singh, Sudhir K.; Ray, Abhijit; Wu, Xiao Hua; Yang, Jin-Ming; Li, Tsai-Kun; Liu, Angela; Liu, Leroy F.; LaVoie, Edmond J. [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 9, p. 2061 - 2073]
[3]Current Patent Assignee: PFIZER INC - US3936461, 1976, A
  • 2
  • [ 28657-75-2 ]
  • [ 109-94-4 ]
  • [ 35478-79-6 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride; sodium methylate In 1,2-dimethoxyethane; water 3 Process for Producing 6,7-Methylenedioxy-4-Quinolone Example 3 Process for Producing 6,7-Methylenedioxy-4-Quinolone 6-Amino-3,4-(methylenedioxy)-acetophenone (5.0 g, 28 mmol) was added to and dissolved in dimethoxyethane (150 ml). To the solution obtained was added sodium methoxide (4.5 g, 84 mmol), and the mixture was stirred at room temperature for 30 minutes. Ethyl formate (12 ml, 143 mmol) was then added, and the mixture was stirred at room temperature for an additional 160 minutes. After adding water (5 ml) to the reaction solution, and stirring for 10 minutes, 10% hydrochloric acid was added to the mixture for neutralization, thereby causing precipitation. The precipitate was collected by filtration, and washed with water (25 ml*2). The product obtained was dried at 40° C. under reduced pressure to give 4.9 g of the desired product (yield 94%). 1H-NMR (DMSO-d6, 500 MHz): δ 5.93 (d, J=7.3 Hz, 1H), 6.12 (s, 2H), 6.97 (s, 1H), 7.38 (s, 1H), 7.75 (d, J=7.3 Hz, 1H), 11.59 (s, 1H). Mass Spectrometry (FD-MS, m/z): 189 (M+).
89% With sodium hydride Heating;
Reference： [1]Current Patent Assignee: KIRIN HOLDINGS CO., LTD.; Kyowa Kirin (in: Kirin Holdings) - US6187926, 2001, B1
[2]Ruchelman, Alexander L.; Houghton, Peter J.; Zhou, Nai; Liu, Angela; Liu, Leroy F.; LaVoie, Edmond J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 3, p. 792 - 804]
  • 3
  • [ 35478-79-6 ]
  • [ 59134-89-3 ]
YieldReaction ConditionsOperation in experiment
91% With trichlorophosphate for 2h; Heating;
83% Stage #1: 6,7-methylenedioxy-4-quinolone With trichlorophosphate for 0.75h; Stage #2: With ammonium hydroxide 4-Chloro-6,7-methylenedioxyquinoline. 6,7-Methylenedioxy-4-quinolone (5.0 g, 26.5 mmol) was boiled in POCl3 (75 mL) for 45 min and then cooled. Excess phospohoryl chloride was removed under reduced pressure and ice water (100 mL) was added to hydrolyze any residual phosphoryl chloride. The mixture was basified (pH 9) with ammonium hydroxide, and the solid precipitate was filtered. This material was extracted into ethyl ether (8 x 100 mL), and the ether solution was dried (MgS04) and evaporated to provide 4.55 g as a white solid, in 83%; mp 127.5-128 °C (lit. mp 129 °C); 1H NMR (CDC13) δ 6.15 (s, 2H), 7.35 (d, 1H, J=4.7), 7.39 (s, 1H), 7.49 (s, 1H), 8.56 (d, 1H, J=4.7); 13C NMR (CDC13) δ 99.8, 102.2, 106.1, 119.9, 123.7, 129.8, 141.2, 147.7, 149.1, 151.4.
Reference： [1]Ruchelman, Alexander L.; Houghton, Peter J.; Zhou, Nai; Liu, Angela; Liu, Leroy F.; LaVoie, Edmond J. [Journal of Medicinal Chemistry, 2005, vol. 48, # 3, p. 792 - 804]
[2]Current Patent Assignee: SANOFI - WO2012/15901, 2012, A1 Location in patent: Page/Page column 49
  • 4
  • [ 35478-79-6 ]
  • [ 529488-28-6 ]
Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 792 - 804
  • 5
  • [ 17394-77-3 ]
  • [ 35478-79-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: PPE / 2 h / 120 °C 2: NaOH / ethanol; H2O / 48 h / Ambient temperature 3: 52 percent / various solvent(s) / 1.5 h / Heating
Reference： [1]Gall-Istok, K.; Sterk, L.; Deak, Gy. [Acta Chimica Hungarica, 1983, vol. 112, # 2, p. 241 - 252]
  • 6
  • [ 369398-78-7 ]
  • [ 1195996-83-8 ]
  • [ 35478-79-6 ]
YieldReaction ConditionsOperation in experiment
In diphenylether at 200℃; for 0.0333333h; Microwave irradiation; Ionic liquid;
Reference： [1]Darque, Albert; Dumetre, Aurelien; Hutter, Sebastien; Casano, Gilles; Robin, Maxime; Pannecouque, Christophe; Azas, Nadine [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 20, p. 5962 - 5964]
  • 7
  • [ 369398-78-7 ]
  • [ 35478-79-6 ]
YieldReaction ConditionsOperation in experiment
With diphenylether at 250℃; for 1.5h;
Reference： [1]Li, Mingzong; Li, Liangxi; Ge, Haibo [Advanced Synthesis and Catalysis, 2010, vol. 352, # 14-15, p. 2445 - 2449]

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