4-((6,7-Dimethoxyquinolin-4-yl)oxy)aniline Chemical Properties

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

Safety Information

HS Code 

2933.49.7000

4-((6,7-Dimethoxyquinolin-4-yl)oxy)aniline Usage And Synthesis

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

4-((6,7-Dimethoxyquinolin-4-yl)oxy)aniline(190728-25-7)Related Product Information

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