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[ CAS No. 190728-24-6 ] {[proInfo.proName]}

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Chemical Structure| 190728-24-6
Chemical Structure| 190728-24-6
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CAS No. :190728-24-6 MDL No. :MFCD22581649
Formula : C17H14N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 326.30 Pubchem ID :-
Synonyms :

Safety of [ 190728-24-6 ]

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

Application In Synthesis of [ 190728-24-6 ]

* 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.

  • Upstream synthesis route of [ 190728-24-6 ]
  • Downstream synthetic route of [ 190728-24-6 ]

[ 190728-24-6 ] Synthesis Path-Upstream   1~3

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  • [ 190728-24-6 ]
  • [ 190728-25-7 ]
YieldReaction ConditionsOperation in experiment
100% With ammonium chloride; zinc In tetrahydrofuran; methanol; water for 2 h; Heating / reflux Step 2:
4-(6,7-dimethoxyquinolin-4-yloxy)aniline (99)
To 98 (0.25 g, 0.77 mmol) in 1:1 MeOH/THF (50 mL) was added Zn dust (0.55 g, 8.4 mmol) and ammonium chloride (0.085 g, 1.6 mmol) in water (5 mL).
The resulting mixture was heated to reflux for 2 h, then filtered through celite and concentrated.
The residue was dissolved in dichloromethane, washed with water, brine, dried (MgSO4), filtered and concentrated to provide crude 99 (0.25 g, >100percent) which was used without further purification. MS (m/z): 297.1 (M+H).
95% With raney nickel In methanol at 30℃; for 10 h; Autoclave Step three:500 ml of methanol was added to the autoclave, and 100 g of intermediate 2 and 25 g of Raney nickel were added.Raise the temperature at 30 ° C for 10 hours;Press filtration, concentration, crystallization, filtration, and drying gave 86 g of Intermediate 3 in a yield of 95percent.
22.4% With palladium 10% on activated carbon; potassium formate In tetrahydrofuran; water at 73℃; for 12 h; To a suspension of 6,7-dimethoxy-4-(4-nitrophenoxy)quinoline (28 g, 85.8 mmol) and HCOOK (50.5 g, 601.1 mmol) in THF (150 niL) and H20 (40 niL) was added Pd/C (2.8 g, 10percent). The reaction was heated to 73 °C for 12 hours, and then cooled to rt. The organic phase was separated and concentrated in vacuo. The residue was stirred in EtOH (90 mL) and 0 (30 mL) overnight and then collected through filtration to give the title compound as a pale yellow solid (5.7 g, 22.4percent). MS (ESI, pos. ion) m/z: 297.1 [M + H]+; NMR (400 MHz, DMSO-i): δ 3.92 (s, 3H), 3.93 (s, 3H), 5.16 (s, 2H), 6.36 (d, J = 5.2 Hz, 1H), 6.65-6.68 (m, 2H), 6.91-6.93 (m, 2H), 7.36 (s, 1H), 7.50 (s, 1H), 8.42 (d, J = 5.3 Hz, 1H).
3.0 kg With formic acid; palladium 10% on activated carbon; potassium formate In tetrahydrofuran; water at 60℃; for 15 h; Large scale Preparation of 4—(6,7 —Dimethoxy—quinoline-4—yloxy)--phenylamine[00258J A solution containing potassium formate (5.0 kg), formic acid (3.0 kg), and water (16.0 kg) was added to a mixture of 6,7-dimethoxy-4-(4-nitro-phenoxy)-quinoline (4.0 kg), 10 percent palladium on carbon (50 percent water wet, 0.4 kg) in tetrahydrofuran (TUF, 40.0 kg) that had been heated to approximately 60 °C. The addition was carried out such that the temperature of the reaction mixture remained approximately 60 °C. When the reaction was deemed complete as determined using in-process HPLC analysis (less than 2 percent starting material remaining, typically 1 5 hours), the reactor contents were filtered. The filtrate was concentrated by vacuum distillation at approximately 35 °C to half of its original volume, which resulted in the precipitation of the product The product was recovered by ifitration, washed with water (12.0 kg), and dried under vacuum at approximately 50 °C to afford the title compound (3.0 kg; 97 percent area under curve (AUC)).
3 kg With formic acid; palladium 10% on activated carbon; potassium formate In tetrahydrofuran; water at 60℃; for 15 h; Large scale Preparation of 4-(6,7-dimethoxy-quinoline-4-yloxy)-phenylamine
A solution containing potassium formate (5.0 kg), formic acid (3.0 kg), and water (16.0 kg) was added to a mixture of 6,7-dimethoxy-4-(4 nitro-phenoxy)-quinoline (4.0 kg), 10percent palladium on carbon (50percent water wet, 0.4 kg) in tetrahydrofuran (40.0 kg) that had been heated to approximately 60° C.
The addition was carried out such that the temperature of the reaction mixture remained approximately 60° C.
When the reaction was deemed complete as determined using in-process HPLC analysis (<2percent starting material remaining, typically 1 5 hours), the reactor contents were filtered.
The filtrate was concentrated by vacuum distillation at approximately 35° C. to half of its original volume, which resulted in the precipitation of the product.
The product was recovered by filtration, washed with water (12.0 kg), and dried under vacuum at approximately 50° C. to afford the title compound (3.0 kg).
3.0 kg With formic acid; palladium 10% on activated carbon; potassium formate In tetrahydrofuran; water at 60℃; for 1.5 h; Large scale Preparation of 4-(6,7 -Dimethoxy-quinoline-4-yloxy)-phenylamine
A solution containing potassium formate (5.0 kg), formic acid (3.0 kg), and water (16.0 kg) was added to a mixture of 6,7-dimethoxy-4-(4-nitro-phenoxy)-quinoline (4.0 kg), 10 percent palladium on carbon (50 percent water wet, 0.4 kg) in tetrahydrofuran (THF, 40.0 kg) that had been heated to approximately 60 °C.
The addition was carried out such that the temperature of the reaction mixture remained approximately 60 °C.
When the reaction was deemed complete as determined using in-process HPLC analysis (less than 2 percent starting material remaining, typically 1 5 hours), the reactor contents were filtered.
The filtrate was concentrated by vacuum distillation at approximately 35 °C to half of its original volume, which resulted in the precipitation of the product.
The product was recovered by filtration, washed with water (12.0 kg), and dried under vacuum at approximately 50 °C to afford the title compound (3.0 kg; 97 percent area under curve (AUC)).
86.3 mg With palladium 10% on activated carbon; hydrogen In N,N-dimethyl acetamide at 30 - 40℃; Autoclave 100 g (0.306 mol) of 6,7-dimethoxy-4-(4-nitrophenoxy) quinoline was treated with 300 g N, N-diethylacetamide was dissolved in an autoclave, and 10percent Pd / C 15g was added to react at 30 to 40 ° C under a hydrogen pressure of 2.8 MPa, and the reaction was complete when no hydrogen was absorbed. After removing most of the solvent, the mixture was poured into 150 ml of water and stirred for 1 hour. The precipitated solid particles were filtered and the cake was washed twice with 100 ml of water, dried at 60 ° C,A solution of 4-(6,7- dimethoxyquinolin-4-oxy)phenylamine (86.3 g), molar yield 95.2percent

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[2] Patent: CN108264482, 2018, A, . Location in patent: Paragraph 0022; 0027
[3] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 23, p. 5117 - 5133
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2018, vol. 61, # 1, p. 11 - 17
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6277 - 6292
[6] Patent: WO2013/180949, 2013, A1, . Location in patent: Paragraph 0172
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[8] Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1359 - 1366
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[10] Patent: WO2010/83414, 2010, A1, . Location in patent: Page/Page column 25
[11] Patent: US2012/70368, 2012, A1,
[12] Patent: US2012/252840, 2012, A1,
[13] Patent: WO2015/164869, 2015, A1, . Location in patent: Paragraph 00255; 00258
[14] Patent: US2016/772, 2016, A1, . Location in patent: Paragraph 0086; 0090
[15] Patent: EP2758057, 2017, B1, . Location in patent: Paragraph 0109
[16] Patent: CN103664778, 2017, B, . Location in patent: Paragraph 0054; 0055; 0056; 0061; 0062
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  • [ 190728-25-7 ]
Reference: [1] Patent: US6143764, 2000, A,
  • 3
  • [ 190728-24-6 ]
  • [ 1140909-48-3 ]
Reference: [1] Patent: WO2015/164869, 2015, A1,
[2] Patent: US2016/772, 2016, A1,
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