8-Aminoisoquinoline Chemical Properties

Melting point:

155-157

Boiling point:

335.7±17.0 °C(Predicted)

Density 

1.210±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

Crystalline Powder

pka

6.20±0.23(Predicted)

color 

Brown

InChI

InChI=1S/C9H8N2/c10-9-3-1-2-7-4-5-11-6-8(7)9/h1-6H,10H2

InChIKey

GUSYANXQYUJOBH-UHFFFAOYSA-N

SMILES

C1C2=C(C=CC=C2N)C=CN=1

CAS DataBase Reference

23687-27-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

Hazard Note 

Harmful/Irritant/Keep Cold

HS Code 

29334900

8-Aminoisoquinoline Usage And Synthesis

Chemical Properties

Brown solid

Uses

8-Aminoisoquinoline and its derivatives are used as intermediates for antimalarial drugs in the pharmaceutical field. For example, their structure is similar to the antimalarial drug primaquine.

Synthesis

General procedure for the synthesis of 8-aminoisoquinolines from 5-bromo-8-nitroisoquinolines: 5-bromo-8-nitroisoquinolines (1.00 g, 3.95 mmol) were dissolved in methanol (70 mL), and hydrogenation was carried out by adding palladium/activated charcoal (10% Pd, 200 mg) as a catalyst for 18 hr at room temperature and atmospheric pressure. Upon completion of the reaction, the reaction mixture was filtered through Celite to remove the catalyst. The filtrate was concentrated and purified by column chromatography (eluent: ethyl acetate/heptane) to afford the target compound 8-aminoisoquinoline (100 mg, 18% yield) as a greenish-brown solid.1H NMR (DMSO-d6, 400 MHz) δ 9.43 (s, 1H), 8.32 (d, 1H), 7.54 (d, 1H), 7.40 (dd, 1H) , 6.99 (d, 1H), 6.72 (d, 1H), 6.22 (s, 2H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 4, p. 803 - 806
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 3, p. 744 - 752
[3] Patent: WO2009/130481, 2009, A1. Location in patent: Page/Page column 143
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4972 - 4982
[5] Patent: WO2006/32851, 2006, A1. Location in patent: Page/Page column 49

8-Aminoisoquinoline(23687-27-6)Related Product Information

• Glucosamine
• EC 2.6.1.2
• Aminopyrine
• Isoquinoline
• Sulfamic acid
• Acetaminophen
• Isoquinoline, 6-iodo- (9CI)
• 8-Iodoisoquinoline
• 8-Iodo quinoline
• pentaquine
• Primaquine diphosphate
• 2-METHYL-8-NITROQUINOLINE
• 2-[(2-amino-5-methylph2-[(2-amino-5-methylphenoxy)methyl]-6-methoxy-8-aminoquinoline-n,n,n',n'-tetraacetic acid tetrapotassium saltenoxy)methyl]-6-methoxy-8-aminoquinoline-n,n,n
• 8-Nitroquinoline
• 8-Aminoquinaldine
• 7-METHYL-8-NITROQUINOLINE
• 6-METHOXY-8-NITROQUINOLINE
• 1-AMINOISOQUINOLINE