2-(2-HYDROXYPHENYL)-4H-1,3-BENZOXAZIN-4-ONE Chemical Properties

Melting point:

204.0 to 208.0 °C

Boiling point:

425.0±47.0 °C(Predicted)

Density 

1.34±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Very Slightly, Heated)

form 

Solid

pka

8.07±0.35(Predicted)

color 

Pale Yellow to Light Yellow

λmax

371nm(H2O)(lit.)

Major Application

pharmaceutical

Safety Information

WGK Germany 

WGK 3

HS Code 

2934999090

Storage Class

11 - Combustible Solids

2-(2-HYDROXYPHENYL)-4H-1,3-BENZOXAZIN-4-ONE Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

Intermediate in the production of Deferasirox.

Synthesis

General procedure for the synthesis of 2-(2-hydroxyphenyl)-4H-benzo[E][1,3]oxazin-4-one from 2-hydroxy-N-(2-hydroxybenzoyl)benzamide: Toluene (1,400 mL) and 10.5 g of p-toluenesulfonic acid monohydrate were added to 140 g of the synthesis intermediate mA, and the reaction mixture was stirred and reacted for 6 hours at 150 °C. Upon completion of the reaction, the mixture was cooled to 60 °C, followed by the addition of 14 mL of triethylamine to the reaction solution and continued cooling to room temperature. The resulting solid was collected by filtration and washed with distilled water to yield 122 g of the synthesized intermediate mB in 94% yield.

References

[1] Patent: EP2460799, 2012, A1. Location in patent: Page/Page column 40-41

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