Isoquinoline-4-carboxylic acid Chemical Properties

Melting point:

264-266 °C

Boiling point:

405.6±18.0 °C(Predicted)

Density 

1.339±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

1.00±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

2933499090

Isoquinoline-4-carboxylic acid Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-isoquinolinecarboxylic acid from 4-cyanoisoquinoline was as follows: potassium hydroxide (20 g, dissolved in 20 mL of water) was added to a stirred solution of 4-cyanoisoquinoline (3.0 g, 19.45 mmol) in ethanol (30 mL) and the reaction mixture was refluxed overnight. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to remove the ethanol. Subsequently, the residue was washed with water and the aqueous layer was extracted with ether (Et2O). The aqueous layer was neutralized with 1N hydrochloric acid and extracted with ethyl acetate (EtOAc). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure to give 4-isoquinolinecarboxylic acid (2 g, 59.3% yield) as an off-white solid.

References

[1] Patent: US2013/178457, 2013, A1. Location in patent: Paragraph 0221
[2] Patent: WO2013/5168, 2013, A2. Location in patent: Page/Page column 40
[3] Journal of the American Chemical Society, 1940, vol. 62, p. 3030
[4] Journal of the American Chemical Society, 1939, vol. 61, p. 183
[5] Archiv der Pharmazie, 2003, vol. 336, # 4-5, p. 258 - 263

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