6-NITROQUINAZOLIN-4(3H)-ONE

6-NITROQUINAZOLIN-4(3H)-ONE Property

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

HazardClass 

IRRITANT

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

6-NITROQUINAZOLIN-4(3H)-ONE Chemical Properties,Usage,Production

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