| Identification | More | [Name]
7-Fluoro-6-nitro-4-hydroxyquinazoline | [CAS]
162012-69-3 | [Synonyms]
4(1H)-QUINAZOLINONE, 7-FLUORO-6-NITRO-
7-FLUORO-6-NITRO-4-HYDROXY-QUINAZOLINE
7-FLUORO-6-NITRO QUINAZOLINONE
7-Fluoro-6-Nitro-4(H)-Quinazoline
6-Nitro-7-Fluoro-4-HydroxyQuinazoline | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C8H4FN3O3 | [MDL Number]
MFCD08458874 | [Molecular Weight]
209.13 | [MOL File]
162012-69-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
282-285 °C(Solv: acetic acid (64-19-7)) | [Boiling point ]
407.6±55.0 °C(Predicted) | [density ]
1.75±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
powder to crystal | [pka]
-2.69±0.20(Predicted) | [color ]
Light yellow to Yellow to Orange | [InChI]
InChI=1S/C8H4FN3O3/c9-5-2-6-4(1-7(5)12(14)15)8(13)11-3-10-6/h1-3H,(H,10,11,13) | [InChIKey]
VTUAEMSZEIGQRM-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C([N+]([O-])=O)C(F)=C2)C(=O)NC=1 | [CAS DataBase Reference]
162012-69-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
7-Fluoro-6-nitroquinazolin-4(3H)-one, is an intermediate in the preparation of kinase inhibitors, such as ATP Site inhibitors of the Tyrosine Kinase activity of the epidermal growth factor receptor. | [Synthesis]
General procedure for the synthesis of 7-fluoro-6-nitro-4-hydroxyquinazoline from 2-amino-4-fluorobenzoic acid: 2-amino-4-fluorobenzoic acid (25 g, 152 mmol) was slowly added dropwise to a mixed solution of concentrated sulfuric acid (50 mL) and concentrated nitric acid (51 mL) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour and then warmed to 110°C and continued stirring for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and quenched by slowly adding ice water (300 mL). The resulting mixture was continued to be stirred for 30 min, followed by filtration to give 7-fluoro-6-nitro-4-hydroxyquinazoline solid product (25 g, 79% yield). The structure of the product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (NMR, 300 MHz, CDCl3) and mass spectrometry (MS, ESI+): NMR data: δ 12.83 (broad single peak, 1H), 8.72 (double peak, 1H), 8.32 (single peak, 1H), 7.79 (double peak, 1H); MS data: m/z 210 [M+H]+. | [References]
[1] Patent: WO2012/30160, 2012, A2. Location in patent: Page/Page column 25
[2] Journal of Medicinal Chemistry, 1996, vol. 39, # 4, p. 918 - 928
[3] Patent: WO2012/182, 2012, A1
[4] Patent: WO2012/356, 2012, A1
[5] Patent: EP2612860, 2013, A1 |
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