4-Aminoisoquinoline Chemical Properties

Melting point:

108.0 to 112.0 °C

Boiling point:

360.0±17.0 °C(Predicted)

Density 

1.210±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

6.29±0.10(Predicted)

color 

White to Brown

InChI

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

InChIKey

ISIUXVGHQFJYHM-UHFFFAOYSA-N

SMILES

C1C2=C(C=CC=C2)C(N)=CN=1

CAS DataBase Reference

23687-25-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933499090

4-Aminoisoquinoline Usage And Synthesis

Uses

4-Isoquinolylamine can be used for synthesis of Rho kinase inhibitors.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 783, 1942 DOI: 10.1021/ja01256a012

Synthesis

A mixture of N-benzyl-4-aminoisoquinoline (1.00 g, 4.27 mmol) was reacted with a mixture of acetic acid (30 mL) and H2SO4 (7.5 mL, concentration not specified) for 6 hours at 100 °C with stirring. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with saturated aqueous NaHCO3 solution. Subsequently, Na2CO3 (200 mL) was added and diluted with water, followed by extraction with EtOAc (5 x 25 mL). The organic phases were combined, concentrated and the residue was purified by chromatography (eluent: EtOAc) to afford the target compound 4-aminoisoquinoline (325 mg, 53% yield) as a yellow solid.1H NMR (DMSO-d6, 400 MHz) δ 8.49 (s, 1H), 8.10 (d, 1H), 7.90 (d, 1H), 7.87 (s, 1H ), 7.64-7.54 (m, 2H), 5.82 (s, 2H).

Solubility in organics

4-isoquinolamine (4-Aminoisoquinoline) is slightly soluble in water and more soluble in organic solvents such as ethanol, dimethylformamide and dichloromethane.

References

[1] Patent: WO2006/32851, 2006, A1. Location in patent: Page/Page column 49

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