8-methylquinazoline-2,4(1H,3H)-dione

8-methylquinazoline-2,4(1H,3H)-dione Property

Melting point:

283 °C

Density 

1.280±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

11.13±0.20(Predicted)

Appearance

Off-white to light yellow Solid

Safety

HS Code 

2933599590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

8-methylquinazoline-2,4(1H,3H)-dione Chemical Properties,Usage,Production

Synthesis

GENERAL METHOD: 2-Amino-3-methylbenzoic acid (5.0 g, 33.1 mmol) was mixed with urea (20 g) and the reaction was stirred at 160°C for 6 hours. Upon completion of the reaction, the reaction mixture was cooled to 100 °C and an equal volume of water was slowly added with continuous stirring for 5 min. Subsequently, the precipitate formed was collected by filtration and washed with cold water to obtain a solid filter cake. This filter cake was suspended in 0.5 N NaOH aqueous solution, heated to boiling and held for 5 minutes, then cooled to room temperature. The pH of the suspension was adjusted to 2 with concentrated hydrochloric acid and the quinazoline dione product was collected by filtration. The product was washed with a mixture of water: methanol (1:1) and dried under vacuum to give 4.50 g (25.5 mmol, 77% yield) of 2,4-dihydroxy-8-methylquinazoline solid. The 1H-NMR (CDCl3) data of the product were as follows: δ (ppm) 7.78-7.74 (m, 1H), 7.49-7.46 (m, 1H), 7.11-7.05 (m, 1H), 2.31 (s, 3H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 461 - 467
[2] Synthesis (Germany), 2016, vol. 48, # 8, p. 1226 - 1234
[3] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 3, p. 254 - 259
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156
[5] Patent: US2016/90374, 2016, A1. Location in patent: Paragraph 0170; 0171