| Identification | More | [Name]
6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one | [CAS]
179688-52-9 | [Synonyms]
6-HYDROXY-7-METHOXY-3,4-DIHYDROQUINAZOLIN-4-ONE
6-Hydroxy-7-Methoxyquinazoline-4-One
6-hydydroxy-7-methoxyquinazoline-4-one
6-Hydroxy-7-methoxy-3H-quinazolin-4-one
7-METHOXYQUINAZOLINE-4,6-DIOL | [EINECS(EC#)]
634-959-7 | [Molecular Formula]
C9H8N2O3 | [MDL Number]
MFCD07787563 | [Molecular Weight]
192.17 | [MOL File]
179688-52-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
293 °C | [Boiling point ]
420.0±55.0 °C(Predicted) | [density ]
1.47±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
powder to crystal | [pka]
9.39±0.20(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C9H8N2O3/c1-14-8-3-6-5(2-7(8)12)9(13)11-4-10-6/h2-4,12H,1H3,(H,10,11,13) | [InChIKey]
OKZIRNNFVQCDSA-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(O)C(OC)=C2)C(=O)NC=1 | [CAS DataBase Reference]
179688-52-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
6-Hydroxy-7-methoxy-4(1H)-quinazolinone is a reactant used in the preparation of 4-anilinoquinazoline derivatives that have shown antitumor activities. 6-Hydroxy-7-methoxy-4(1H)-quinazolinone was also used as a reactant in the synthetic preparation of 2-arylbenzothiazoles as kinase inhibitors. | [Synthesis]
General procedure for the synthesis of 6-hydroxy-7-methoxyquinazolin-4-one from 6,7-dimethoxyquinazolin-4-one:
1. 3.06 g of 6,7-dimethoxyquinazolin-4-one was dissolved in 20 mL of methanesulfonic acid.
2. 2.66 g of L-methionine was added to the above solution and the reaction was stirred at 100 °C for 22 hours.
3. Upon completion of the reaction, ice was added to the reaction mixture and neutralized with 40% aqueous sodium hydroxide solution to pH neutral to promote crystallization of the product.
4. The solid product was collected by filtration under reduced pressure, washed with water and subsequently air dried to afford 6-hydroxy-7-methoxyquinazolin-4-one (2.67 g, 94% yield).
Product characterization data: 1H-NMR (300MHz, DMSO-d6) δ 11.94 (s, 1H), 9.81 (s, 1H), 7.92 (d, J=Hz, 1H), 7.39 (s, 1H), 7.11 (s, 1H), 3.91 (s, 3H). | [References]
[1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 7, p. 3046 - 3055
[2] Patent: WO2008/150118, 2008, A2. Location in patent: Page/Page column 21
[3] Patent: WO2005/97134, 2005, A2. Location in patent: Page/Page column 13; figure 1
[4] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8551 - 8556
[5] Angew. Chem., 2013, vol. 125, # 33, p. 8713 - 8718,6 |
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