ISOQUINOLINE-5-CARBALDEHYDE

ISOQUINOLINE-5-CARBALDEHYDE Property

Melting point:

116-120 °C

Boiling point:

331.7±15.0 °C(Predicted)

Density 

1.223±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.53±0.13(Predicted)

color 

White to Light yellow

Sensitive 

Air Sensitive

BRN 

112875

InChI

InChI=1S/C10H7NO/c12-7-9-3-1-2-8-6-11-5-4-10(8)9/h1-7H

InChIKey

ILRSABOCKMOFGW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

80278-67-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29334900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

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

ISOQUINOLINE-5-CARBALDEHYDE Chemical Properties,Usage,Production

Chemical Properties

Yellow to light brown powder

Uses

Direct conversion of heteroaryl-carboxaldehydes to acetonitriles by treatment with cyanoethylphosphonate followed by samarium(II) iodide reduction.

Synthesis

To a solvent mixture of ether (80 mL) and tetrahydrofuran (80 mL), n-butyllithium (19.3 mL, 2.5 M hexane solution, 48 mmol) was slowly added dropwise at -78 °C. Subsequently, a solution of 5-bromoisoquinoline (5.0 g, 24 mmol) in tetrahydrofuran (10 mL) was added dropwise. The reaction mixture was stirred at -78 °C and under argon protection for 30 min. Referring to the method of Pearson et al. in Journal of Heterocyclic Chemistry, Vol. 6, No. 2, pp. 243-245 (1969), a tetrahydrofuran (10 mL) solution of N,N-dimethylformamide (3.30 g, 45 mmol) was rapidly added to the lithium isoquinolinium solution after it was cooled to -78°C. The mixture was continued to be stirred at -78 °C for 15 minutes. Subsequently, ethanol (20 mL) and saturated ammonium chloride solution were added. The resulting suspension was slowly warmed to room temperature. The organic and ether extracted layers were combined and dried with anhydrous sodium sulfate. Purification by silica gel column chromatography (SiO2-H, hexane solution of 50% ethyl acetate) and ethanol recrystallization afforded isoquinoline-5-carbaldehyde (2.4 g, 15 mmol, 64% yield) as a light yellow solid with a melting point of 114-116 °C.1H NMR (DMSO-d6) δ 10.40 (s, 1H), 9.44 (s, 1H), 8.85 (d 1H, J = 6.0 Hz), 8.69 (d, 1H, J = 6.0 Hz), 8.45 (m, 2H), 7.90 (t, 1H, J = 7.2 Hz); 13C NMR (DMSO-d6) δ 194.23, 153.5, 146.2, 140.2, 135.2, 132.6, 130.2, 128.6, 127.5, 117.2. Calculated elemental values (C10H7NO-0.05H2O): C, 75.99; H, 4.53; N, 8.86. Measured values: C, 75.98; H, 4.66; N, 8.68.

References

[1] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3660 - 3668
[2] Patent: US2007/155720, 2007, A1. Location in patent: Page/Page column 24