7-AMINO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE Chemical Properties

Melting point:

123-125 °C

Boiling point:

495.9±45.0 °C(Predicted)

Density 

1.237±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

crystalline solid

pka

14.96±0.20(Predicted)

color 

Amber/tan

Safety Information

HS Code 

2933499090

7-AMINO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE Usage And Synthesis

Uses

7-Amino-3,4-dihydro-2H-isoquinolin-1-one is used as a reactant in the preparation of dihydroisoquinolinones as potent inhibitors of poly(ADP-?ribose) polymerase.

Synthesis

General procedure for the synthesis of 7-amino-3,4-dihydroisoquinolin-1(2H)-one from 7-nitro-3,4-dihydroisoquinolin-1(2H)-one: 7-nitro-3,4-dihydroisoquinolin-1(2H)-one (700 mg, 3.6 mmol) was dissolved in methanol (25 mL), and 10% palladium/carbon catalyst (catalytic amount) was added. The reaction was stirred under hydrogen (60 psi) atmosphere for 1 hour. Upon completion of the reaction, the mixture was filtered through diatomaceous earth to remove the catalyst and the filtrate was concentrated under vacuum to afford 7-amino-3,4-dihydroisoquinolin-1(2H)-one (500 mg, 86% yield). The product was characterized by 1H NMR (400 MHz, CD3OD): δ 2.81 (t, J = 6.59 Hz, 2H), 3.42 (t, J = 6.55 Hz, 2H), 6.84 (dd, J = 8.13,2.42 Hz, 1H), 7.02 (d, J = 7.91 Hz, 1H), 7.26 (d, J = 2.64 Hz, 1H ).

References

[1] Journal of Organic Chemistry, 1983, vol. 48, # 19, p. 3220 - 3234
[2] Patent: WO2008/79759, 2008, A1. Location in patent: Page/Page column 98
[3] Patent: WO2008/79836, 2008, A2. Location in patent: Page/Page column 86
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2799 - 2808
[5] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1077 - 1081

7-AMINO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(66491-03-0)Related Product Information

• 3,4-Dihydro-2H-isoquinolin-1-one
• 3-DIFLUOROMETHYL-7-NITRO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• 7-NITRO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• 7-AMINO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• 7-AMINO-4H-ISOQUINOLINE-1,3-DIONE
• 7-ETHOXYCARBONYLAMINO-1-OXO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
• 3-(FLUOROMETHYL)-3,4-DIHYDRO-7-NITROISOQUINOLIN-1(2H)-ONE