4-Hydroxy-6,7-dimethoxyqunioline Chemical Properties

Melting point:

227.0 to 231.0 °C

Boiling point:

370.9±37.0 °C(Predicted)

Density 

1.257±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

powder to crystal

pka

4.26±0.40(Predicted)

color 

Light orange to Yellow to Green

InChI

InChI=1S/C11H11NO3/c1-14-10-5-7-8(6-11(10)15-2)12-4-3-9(7)13/h3-6H,1-2H3,(H,12,13)

InChIKey

QOGPNCUTXVZQSL-UHFFFAOYSA-N

SMILES

N1C2C(=CC(OC)=C(OC)C=2)C(O)=CC=1

CAS DataBase Reference

13425-93-9(CAS DataBase Reference)

Safety Information

HS Code 

2933.49.7000

HazardClass 

IRRITANT

4-Hydroxy-6,7-dimethoxyqunioline Usage And Synthesis

Appearance

4-Hydroxy-6,7-dimethoxyqunioline is a slightly pale yellow to yellow solid.

Uses

4-Hydroxy-6,7-dimethoxyqunioline, also called 6,7-Dimethoxy-4-quinolinol was used in the study of synthesis of ring-substituted 4-aminoquinolines and evaluation fo their antimalarial activities.

Synthesis

General procedure for the synthesis of 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylic acid from ethyl 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylate: ethyl 4-hydroxy-6,7-dimethoxyquinoline-3-carboxylate (700 mg, 2.53 mmol) was added to potassium hydroxide (450 mg, 7.6 mmol) dissolved in 20 mL of H2O/EtOH (1:1, v /v) solution. The mixture was placed in a sealed container (XP-500 Plus container) and heated using microwaves (MARS 5 Microwave System) at 180°C, 260-280 psi pressure for 50 min. Upon completion of the reaction, the mixture was cooled to room temperature and transferred to a flask. Subsequently, the solution was acidified to pH about 6 with acetic acid (about 2 mL), saturated with sodium chloride, and extracted with tetrahydrofuran (3 x 100 mL). The organic layers were combined, washed with brine and concentrated to give 6,7-dimethoxyquinolin-4-ol in 90% yield.1H NMR (400 MHz, DMSO-d6) δ ppm: 3.81 (s, 3H), 3.84 (s, 3H), 5.93 (d, J=7.3 Hz, 1H), 7.05 (s, 1H), 7.42 (s, 1H), and 7.76 (d, J=7.3 Hz, 1H).

storage

Store at room temperature.

References

[1] Patent: WO2005/121125, 2005, A1. Location in patent: Page/Page column 41-42
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1264

4-Hydroxy-6,7-dimethoxyqunioline(13425-93-9)Related Product Information

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