7-BENZYLOXY-4-HYDROXY-QUINOLINE Chemical Properties

Boiling point:

455.8±30.0 °C(Predicted)

Density 

1.256±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.12±0.40(Predicted)

form 

solid

color 

Tan/brown

InChI

InChI=1S/C16H13NO2/c18-16-8-9-17-15-10-13(6-7-14(15)16)19-11-12-4-2-1-3-5-12/h1-10H,11H2,(H,17,18)

InChIKey

KWQRHYWEGFFXKV-UHFFFAOYSA-N

SMILES

N1C2C(=CC=C(OCC3=CC=CC=C3)C=2)C(O)=CC=1

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2933499090

7-BENZYLOXY-4-HYDROXY-QUINOLINE Usage And Synthesis

Synthesis

Step 2) Synthesis of 7-(benzyloxy)quinolin-4-ol: 5-((3-(benzyloxy)phenylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (300 g, 849.8 mmol) was dissolved in 1,2-dichlorobenzene (3 L) and heated to reflux for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature, followed by further cooling in an ice bath for 2 hours. The precipitated solid was collected by filtration and the solid was stirred with methanol (300 mL) for 2 hours at room temperature. The solid was collected by filtration again and dried under vacuum at 45 °C to afford the title compound 7-(benzyloxy)quinolin-4-ol as a light colored solid (103 g, 48.5% yield). Mass spectrum (ESI, positive ion mode) m/z: 252.2 [M + H]+; 1H NMR (400 MHz, DMSO-d6) δ: 5.23 (s, 2H), 5.98 (d, J = 7.2 Hz, 1H), 7.02 (t, 2H), 7.41 (t, 1H), 7.45 (t, J = 6.8 Hz, 2H), 7.52 (d J = 7.6Hz, 2H), 7.84 (t, J = 6.4Hz, 1H), 8.03 (d, J = 9.2Hz, 1H), 11.60 (s, 1H).

References

[1] Patent: US2012/219522, 2012, A1. Location in patent: Page/Page column 20