| Identification | More | [Name]
6-Hydroxy-2(1H)-3,4-dihydroquinolinone | [CAS]
54197-66-9 | [Synonyms]
3,4-DIHYDRO-6-HYDROXY-2(1H)-QUINOLINONE
3,4-DIHYDRO-6-HYDROXYQUINOLINONE
6-HQ
6-HYDROXY-1,2,3,4-TETRAHYDRO-2-QUINOLINONE
6-HYDROXY-2(1H)-3,4-DIHYDROQUINOLINONE
6-HYDROXY-2-OXO-1,2,3,4-TETRAHYDROQUINOLINE
6-HYDROXY-3,4-DIHYDRO-1H-QUINOLIN-2-ONE
6-HYDROXY-3,4-DIHYDRO-2(1H)-QUINOLINONE
6-HYDROXY-3,4-DIHYDRO-2-QUINOLINONE
6-HYDROXY-3,4-DIHYDROCARBOSTYRIL
6-HYDROXY-3,4-DIHYDROCARBSTYRIL
6-HYDROXY-3,4-DIHYDROQUINOLIN-2(1H)-ONE
6-HYDROXY-3,4-DIHYDROQUINOLONE
6-HYDROXYL-3,4-DIHYDROCARBOSTYRIL
AURORA KA-4814
6-HYDROXY-2-OXO-1,2,3,4-TETRAHYDROQUINOLINE (6-HQ)
6-Hydroxyl-3.4-dihydro-2-(1H)-quinolinone
Intermediate of Cilostazol
Q-2
3,4-Dihydro-6-hydroxy-2-(IH)-quinolinone | [EINECS(EC#)]
611-111-4 | [Molecular Formula]
C9H9NO2 | [MDL Number]
MFCD02179410 | [Molecular Weight]
163.17 | [MOL File]
54197-66-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white solid | [Melting point ]
236-240 °C | [Boiling point ]
424.5±45.0 °C(Predicted) | [density ]
1.282±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly, Heated) | [form ]
neat | [pka]
9.86±0.20(Predicted) | [color ]
White to Almost white | [Usage]
A metabolite of Cilostazole. | [InChI]
InChI=1S/C9H9NO2/c11-7-2-3-8-6(5-7)1-4-9(12)10-8/h2-3,5,11H,1,4H2,(H,10,12) | [InChIKey]
HOSGXJWQVBHGLT-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(O)C=C2)CCC1=O | [CAS DataBase Reference]
54197-66-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
2933790002 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white solid | [Uses]
A metabolite of Cilostazole. | [Synthesis]
2) 98 g of 3-chloro-N-(4-methoxyphenyl)acrylamide obtained from step 1) was mixed with N-(4-methoxyphenyl)-3-chloroacrylamide, 500 mL of tetrahydrofuran and 98 g of palladium chloride. The reaction mixture was heated to 100 °C under 5 MPa pressure and maintained at that temperature. Upon completion of the reaction, it was cooled to room temperature and then maintained at 110°C for 3 hours. Subsequently, filtration was performed and the filtrate was rotary evaporated to dryness to obtain 6-hydroxy-3,4-dihydro-2(1H)-quinolone crude.3) The 6-hydroxy-3,4-dihydro-2(1H)-quinolone crude obtained in step 2) was dissolved in 50 mL of ethanol, recrystallized and decolorized using activated carbon. After filtration, 74 g of 6-hydroxy-3,4-dihydro-2(1H)-quinolinone was obtained as an off-white solid in 95% yield. The total yield was 85%. | [References]
[1] Patent: CN108383781, 2018, A. Location in patent: Paragraph 0033; 0034
[2] Patent: CN107325078, 2017, A. Location in patent: Paragraph 0039-0040; 0043-0044; 0046-0047; 0049-0050; 0052
[3] Journal of the Chinese Chemical Society, 2000, vol. 47, # 1, p. 155 - 162
[4] Heterocycles, 2009, vol. 78, # 1, p. 189 - 195
[5] Asian Journal of Chemistry, 2011, vol. 23, # 4, p. 1655 - 1660 |
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