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

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

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

HS Code 

2933499090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

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