| Identification | Back Directory | [Name]
BenzenaMine, 4-[(6,7-diMethoxy-4-quinolinyl)oxy]- | [CAS]
190728-25-7 | [Synonyms]
4-(6,7-Dimethoxy-quinoL
Intermediate 1 of Cabozantinib
Cabozantinib Genotoxic Impurity I
4-[(6,7-dimethoxy-4-quinolinyl)oxy]-
4-(6,7-dimethoxy quinolinoxy) aniline
4-(4-Aminophenoxy)-6,7-dimethoxyquinoline
6,7-Dimethoxy-4-(4-aminophenoxy)quinoline
4-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline
6,7-Dimethoxy-4-(4-aminophenyloxy)quinolone
4-(2,3-dimethoxynaphthalen-5-yloxy)benzenamine
BenzeMine, 4-[(6,7-diMethoxy-4-quinolinyl)oxy]-
4-[(6,7-diMethoxy-4-quinolinyl)oxy]-BenzenaMine
[4-[(6,7-Dimethoxyquinolin-4-yl)oxy]phenyl]amine
BenzenaMine, 4-[(6,7-diMethoxy-4-quinolinyl)oxy]-
4-[(6,7-dimethoxyquinolin-4-yl)oxy]aniline
4-((6,7-Dimethoxyquinolin-4-yl)oxy)aniline | [Molecular Formula]
C17H16N2O3 | [MDL Number]
MFCD19685633 | [MOL File]
190728-25-7.mol | [Molecular Weight]
296.321 |
| Chemical Properties | Back Directory | [Melting point ]
211.0 to 215.0 °C | [Boiling point ]
481.8±45.0 °C(Predicted) | [density ]
1.246±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly, Sonicated), Methanol (Slightly) | [form ]
powder to crystal | [pka]
6.79±0.30(Predicted) | [color ]
Light yellow to Brown | [InChI]
InChI=1S/C17H16N2O3/c1-20-16-9-13-14(10-17(16)21-2)19-8-7-15(13)22-12-5-3-11(18)4-6-12/h3-10H,18H2,1-2H3 | [InChIKey]
VXEQRXJATQUJSN-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=C(OC2C3C(N=CC=2)=CC(OC)=C(OC)C=3)C=C1 |
| Hazard Information | Back Directory | [Uses]
4-(6,7-Dimethoxy-Quinolin-4-Yloxy)-Phenylamine is used in preparation of Cabozantinib Defluorination impurity. | [Chemical Reactivity]
4-((6,7-Dimethoxyquinolin-4-yl)oxy)aniline is a primary alcohol that has been shown to catalyze the reaction of potassium carbonate with an alkali metal hydroxide to produce potassium. It has also been shown to be a base catalyst for the reaction of cyclopropanecarboxylic acid with an alcohol ester to produce high yield.
| [Synthesis]
Step 2: Synthesis of 4-[(6,7-dimethoxyquinolin-4-yl)oxy]aniline (99)
To a 1:1 MeOH/THF (50 mL) mixed solvent of 6,7-dimethoxy-4-(4-nitrophenoxy)quinoline (98) (0.25 g, 0.77 mmol) was added a solution of zinc powder (0.55 g, 8.4 mmol) and ammonium chloride (0.085 g, 1.6 mmol) in water (5 mL). The reaction mixture was heated to reflux for 2 hours. Upon completion of the reaction, the insoluble material was removed by diatomaceous earth filtration and the filtrate was concentrated under reduced pressure. The concentrated residue was dissolved in dichloromethane, washed sequentially with water and saturated saline, and the organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product 99 (0.25 g, >100% yield), which can be used directly in the next reaction without further purification. Mass spectrometry (MS) data: m/z 297.1 ([M+H]+). | [References]
[1] Patent: US2008/4273, 2008, A1. Location in patent: Page/Page column 86
[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 |
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