6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE Chemical Properties

Melting point:

174-176 °C

Boiling point:

423.0±45.0 °C(Predicted)

Density 

1.237±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

14.47±0.20(Predicted)

Appearance

Light yellow to light brown Solid

Safety Information

HS Code 

2933499090

6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE Usage And Synthesis

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

6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(22246-13-5)Related Product Information

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