6-AMINO-3H-QUINAZOLIN-4-ONE Chemical Properties

Melting point:

303 °C(Solv: water (7732-18-5))

Boiling point:

421.1±47.0 °C(Predicted)

Density 

1.49±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

3.95±0.20(Predicted)

Appearance

Light yellow to yellow Solid

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

6-AMINO-3H-QUINAZOLIN-4-ONE Usage And Synthesis

Synthesis

General procedure for the synthesis of 6-amino-3H-quinazolin-4-one from 4-hydroxy-6-nitroquinazoline: a methanol (500 ml) solution of intermediate 5A (1 g, 5.23 mmol) was added to a 1 L three-necked flask to form a yellow suspension. Subsequently 10% palladium/carbon catalyst (0.056 g, 0.523 mmol) was added. The reaction mixture was stirred at room temperature and reacted for 4 hours under hydrogen balloon atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to give 0.84 g of yellow solid product (100% yield). The structure of the product was confirmed by 1H NMR (500 MHz, DMSO-d6) with chemical shifts δppm of 5.60 (s, 2H), 7.05 (dd, J = 8.80,2.75Hz, 1H), 7.16 (d, J = 2.75Hz, 1H), 7.36 (d, J = 8.80Hz, 1H), 7.74 (s, 1H ) and 11.80 (s, 1H).

References

[1] Patent: WO2008/79759, 2008, A1. Location in patent: Page/Page column 90
[2] Patent: WO2008/79836, 2008, A2. Location in patent: Page/Page column 86
[3] Tetrahedron Letters, 2003, vol. 44, # 24, p. 4455 - 4458
[4] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[5] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 12, p. 1166 - 1172

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