6-NITROQUINAZOLIN-4(3H)-ONE Chemical Properties

Melting point:

286-287 °C

Boiling point:

407.0±47.0 °C(Predicted)

Density 

1?+-.0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

-1.01±0.20(Predicted)

color 

Yellow

InChI

InChI=1S/C8H5N3O3/c12-8-6-3-5(11(13)14)1-2-7(6)9-4-10-8/h1-4H,(H,9,10,12)

InChIKey

MOBNCKURXDGQCB-UHFFFAOYSA-N

SMILES

N1C2=C(C=C([N+]([O-])=O)C=C2)C(=O)NC=1

Safety Information

HazardClass 

IRRITANT

6-NITROQUINAZOLIN-4(3H)-ONE Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

Intermediate in the preparation of anticancer agents and enzyme inhibitors.

Synthesis

1. Preparation of 6-nitro-3H-quinazolin-4-one: 150 g of 2-amino-5-nitrobenzoic acid was added to 200 ml of formamide and stirred until completely dissolved. The reaction mixture was heated to 170°C and maintained at this temperature for 4 hours. After completion of the reaction, the mixture was cooled to 100°C. 500 ml of ice water was slowly added and stirring was continued for 1 hour. Subsequently, the mixture was filtered under reduced pressure and the solid product was collected. The solid was washed with plenty of water to remove residual reactants and by-products. Finally, the resulting solid was dried at 40 °C for 15 h to afford 4-hydroxy-6-nitroquinazoline (140 g, 90% yield). The structure of the product was confirmed by 1H-NMR (DMSO-d6, 300 MHz): δ8.77 (d, J = 2.7 Hz, 1H), 8.55 (dd, J = 6.9 Hz, 1H), 8.36 (s, 1H), 7.84 (d, J = 9 Hz, 1H).

References

[1] Patent: WO2006/71017, 2006, A1. Location in patent: Page/Page column 34
[2] Tetrahedron Letters, 2002, vol. 43, # 21, p. 3911 - 3913
[3] Tetrahedron Letters, 2003, vol. 44, # 24, p. 4455 - 4458
[4] Patent: US2005/187231, 2005, A1. Location in patent: Page/Page column 14
[5] Tetrahedron, 2013, vol. 69, # 15, p. 3182 - 3191

6-NITROQUINAZOLIN-4(3H)-ONE(6943-17-5)Related Product Information

• 6-NITROQUINAZOLIN-4(3H)-ONE
• 7-Fluoro-6-nitro-4-hydroxyquinazoline
• 2,4-DIHYDROXY-6-NITROQUINAZOLINE
• 6-Nitro-7-Chloro-4-HydroxyQuinazoline
• 2-AMINO-6-NITRO-4(3H)-QUINAZOLONE
• 2-[(3,4-DICHLOROPHENYL)AMINO]-1,4-DIHYDRO-6-NITRO-4-OXO-N-2-PROPENYL-8-QUINAZOLINECARBOXAMIDE
• 7-FLUORO-6-NITROQUINAZOLIN-4(3H)-ONE
• 2-mercapto-7-nitroquinazolin-4(3H)-one
• 3-ethyl-2-mercapto-7-nitroquinazolin-4(3H)-one
• 2-[4-Methyl-1-piperazinyl]-6-nitroquinazolin-4(3H)-one
• 2-[4-Methyl-1-piperazinyl]-7-nitroquinazolin-4(3H)-one
• 2-Methyl-6-nitroquinazolin-4(3H)-one
• 3-ethyl-2-mercapto-6-nitroquinazolin-4(3H)-one
• 7-MORPHOLIN-4-YL-6-NITROQUINAZOLIN-4(3H)-ONE
• 2-mercapto-6-nitroquinazolin-4(3H)-one
• 7-(METHYLAMINO)-6-NITROQUINAZOLIN-4(3H)-ONE
• 7-CHLORO-6-NITROQUINAZOLIN-4(3H)-ONE
• 2-mercapto-3-methyl-6-nitroquinazolin-4(3H)-one