| Identification | More | [Name]
6,7-Dihydro-5H-quinolin-8-one | [CAS]
56826-69-8 | [Synonyms]
6,7-DIHYDRO-5H-QUINOLIN-8-ONE
6,7-DIHYDRO-5H-QUINOLINE-8-ONE
6,7-DIHYDROQUINOLIN-8(5H)-ONE
AKOS BB-8709
6,7-DIHYDRO-5H-QUINOLIN-8-ONE,99+%
6,7-dihydro-5H-quinolin-8-one98%+, | [EINECS(EC#)]
225-682-9 | [Molecular Formula]
C9H9NO | [MDL Number]
MFCD03839916 | [Molecular Weight]
147.17 | [MOL File]
56826-69-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
96-98 °C(Solv: isopropyl ether (108-20-3)) | [Boiling point ]
140 °C(Press: 0.1 Torr) | [density ]
1.168±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 10 mg/ml | [form ]
A crystalline solid | [pka]
3.46±0.20(Predicted) | [InChI]
InChI=1S/C9H9NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h2,4,6H,1,3,5H2 | [InChIKey]
JIAKIQWNYAZUJD-UHFFFAOYSA-N | [SMILES]
N1C2=C(CCCC2=O)C=CC=1 | [CAS DataBase Reference]
56826-69-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
6,7-Dihydro-5H-quinolin-8-one is a synthetic intermediate.1,2 It has been used in the synthesis of tetrahydropyridoazepinones and thiosemicarbazones with anticancer activity. | [Chemical Properties]
light yellow crystalline | [Uses]
6,7-Dihydroquinolin-8(5H)-one is a synthetic intermediate useful for pharmaceutical synthesis. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 49, p. 2208, 1984 DOI: 10.1021/jo00186a027
Synthetic Communications, 33, p. 3497, 2003 DOI: 10.1081/SCC-120024729 | [Synthesis]
Preparation of 6,7-dihydro-5H-quinolin-8-one: 8-hydroxy-5,6,7,8-tetrahydroquinoline (13.96 g, 93.6 mmol) was dissolved in anhydrous dichloromethane (400 mL) under stirring conditions. Subsequently, activated manganese dioxide (85% pure, 82.22 g, 804 mmol) was added to this solution. The resulting non-homogeneous mixture was stirred for 18 hours. Upon completion of the reaction, the black slurry was filtered through a diatomaceous earth filter cake and the cake was washed with dichloromethane (3 x 50 mL). The washes were combined and concentrated to afford 11.27 g (82% yield) of the target product, 6,7-dihydro-5H-quinolin-8-one, as a light yellow solid, which could be used in subsequent reactions without further purification. The structure of the product was characterized by 1H NMR (CDCl3) δ 2.17-2.25 (m, 2H), 2.82 (t, 2H, J = 7 Hz), 3.04 (t, 2H, J = 6 Hz), 7.37 (dd, 1H, J = 9,6 Hz), 7.66 (dd, 1H, J = 9,1 Hz), 8.71 (dd, 1H, J = 6,1 Hz); 13C NMR (CDCl3) δ 22.2, 28.6, 39.2, 126.6, 137.3, 140.5, 147.6, 148.6, 196.5 confirmed.ES-MS m/z 148 (M + H) further validated the product structure. | [References]
[1] Patent: US2003/220341, 2003, A1. Location in patent: Page/Page column 9
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 213 - 220
[3] Patent: US2004/19058, 2004, A1 |
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