| Identification | Back Directory | [Name]
6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE | [CAS]
22246-13-5 | [Synonyms]
AKOS BB-9801
6-amino-3,4-dihydrocarbostyril
6-Amino-3,4-dihydroquinolin-2(1H)
6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE
6-AMINO-3,4-DIHYDRO-2(1H)-QUINOLINONE
6-amino-3,4-dihydro-2(1 )-quinalinone
6-AMino-1,3,4-trihydro-quinolin-2-one
6-aMino-3,4-dihydro-2(1H )-quinalinone
6-Amino-3,4-dihydroquinoline-2(1H)-one
2(1H)-Quinolinone, 6-amino-3,4-dihydro- | [Molecular Formula]
C9H10N2O | [MDL Number]
MFCD00559318 | [MOL File]
22246-13-5.mol | [Molecular Weight]
162.19 |
| Chemical Properties | Back Directory | [Melting point ]
174-176 °C | [Boiling point ]
423.0±45.0 °C(Predicted) | [density ]
1.237±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [pka]
14.47±0.20(Predicted) | [Appearance]
Light yellow to light brown Solid |
| Hazard Information | Back Directory | [Uses]
6-Amino-3,4-dihydrocarbostyril is a useful synthetic compound used to prepare cardiotonic agents. | [Synthesis]
At 0 °C, 6-nitro-3,4-dihydroquinolin-2(1H)-one (3 g) was dissolved in methanol (60 mL) and zinc powder (5 eq.) and ammonium chloride (5 eq.) were added sequentially. The reaction mixture was stirred at room temperature for 1 h. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was filtered through a bed of diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was dissolved in a dichloromethane solution containing 5% methanol and subsequently washed with water. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 6-amino-3,4-dihydroquinolin-2(1H)-one (2.3 g in 91% yield. The product was characterized by 1H NMR (DMSO-d6, 400MHz): δ 9.654 (broad single peak, 1H), 6.53 (double peak, 1H), 6.378-6.334 (multiple peaks, 2H), 4.707 (broad single peak, 2H), 2.699 (triple peak, 2H), 2.330 (triple peak, 2H). | [References]
[1] Patent: WO2015/38417, 2015, A1. Location in patent: Page/Page column 90; 91
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4606 - 4609
[3] Patent: WO2006/71940, 2006, A2. Location in patent: Page/Page column 416
[4] Proceedings of the Imperial Academy (Tokyo), 1939, vol. 15, p. 148,153
[5] Chem. Zentralbl., 1939, vol. 110, # II, p. 3089 |
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