6-AMINOISOQUINOLINE Chemical Properties

Melting point:

211-212 °C(Solv: benzene (71-43-2))

Boiling point:

343.1±15.0 °C(Predicted)

Density 

1.210±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMF (Slightly), DMSO (Sparingly), Methanol (Slightly)

pka

7.10±0.10(Predicted)

form 

solid

color 

Light yellow to yellow

InChI

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

InChIKey

NGFCTYXFMDWFRQ-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26

HS Code 

2933499090

6-AMINOISOQUINOLINE Usage And Synthesis

Description

6-Aminoisoquinoline is an organosynthetic intermediate used in the preparation of Netarsudil, which is a drug used in the treatment and management of glaucoma and high intraocular pressure.

Uses

6-Aminoisoquinoline is a reactant used in the preparation of N-[{2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)-pyridin-3-yl}methyl] N''-(6,6-fused heterocyclic) ureas as highly potent TRPV1 antagonists.

Synthesis

General procedure for the synthesis of 6-aminoisoquinoline from 6-bromoisoquinoline: 17.2 g of 6-bromoisoquinoline (see WO 2008/077553), 200 mL of 28% ammonia solution and 10.8 g of copper (II) sulfate pentahydrate were placed in an autoclave and sealed. The mixture was stirred and reacted at 190 °C for 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction solution was poured into 250 mL of 10% aqueous sodium hydroxide solution and extracted with ethyl acetate (100 mL each time, 5 times). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was suspended with dichloromethane and filtered to give 10.2 g of light brown crystalline 6-aminoisoquinoline in 85% yield.1H-NMR spectrum (CDCl3, δ ppm): 5.54 (broad single peak, 2H), 6.58 (single peak, 1H), 7.00 (double peak, J = 9.0 Hz, 1H), 7.35 (double peak, J = 5.5 Hz, 1H), 7.75 (double peak, J = 5.5 Hz, 1H). 7.75 (double peak, J = 9.0 Hz, 1H), 8.32 (double peak, J = 5.5 Hz, 1H), 8.98 (single peak, 1H).

References

[1] Patent: US2012/35159, 2012, A1. Location in patent: Page/Page column 8

6-AMINOISOQUINOLINE(23687-26-5)Related Product Information

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