3-isoquinolinecarboxaldehyde Chemical Properties

Melting point:

47 °C

Boiling point:

151 °C(Press: 10 Torr)

Density 

1.223±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

2.94±0.30(Predicted)

color 

White

InChI

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

InChIKey

XOYMAJLARWXZBA-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933499090

3-isoquinolinecarboxaldehyde Usage And Synthesis

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 688, 1951 DOI: 10.1021/ja01146a055

Synthesis

General procedure for the synthesis of isoquinoline-3-carbaldehyde from methyl isoquinoline-3-carboxylate: methyl isoquinoline-3-carboxylate (2.0 g, 10.7 mmol) was dissolved in toluene and the solution was cooled to -78 °C. Diisobutylaluminum hydride (1 M solution in toluene, 21.4 mL, 21.4 mmol) was slowly added to this solution using a syringe over a period of 15 minutes. Keeping the reaction mixture at -78 °C, the reaction was quenched with a mixture of ether (80 mL), acetic acid (20 mL) and water (8 mL). The mixture was then slowly warmed to room temperature and stirred overnight. The organic layer was separated and the solvent was evaporated. Purification by fast column chromatography (eluent gradient: 1:4 ethyl acetate/hexane to 1:3 ethyl acetate/hexane) afforded 1.1 g of the title compound isoquinoline-3-carbaldehyde in 65% yield.1H-NMR (CDCl3, 300 MHz) δ 10.24 (s, 1H), 9.35 (s, 1H), 8.36 (s, 1H), 8.07- 7.98 (m, 2H), 7.82-7.32 (m, 2H). MS: m/z 158 ([MH]+).

References

[1] Patent: WO2005/56550, 2005, A2. Location in patent: Page/Page column 75-76
[2] Patent: WO2005/92885, 2005, A1. Location in patent: Page/Page column 73
[3] Patent: WO2005/56562, 2005, A1. Location in patent: Page/Page column 71-72
[4] Tetrahedron Letters, 1999, vol. 40, # 6, p. 1211 - 1214
[5] Patent: US5554620, 1996, A

3-isoquinolinecarboxaldehyde(5470-80-4)Related Product Information

• ISOQUINOLINE-3-CARBOXYLIC ACID
• Methyl 3-isoquinolinecarboxylate
• Isoquinoline-1-carboxylic acid
• 5-HYDROXYMETHYLISOQUINOLINE
• 1-ISOQUINOLINEMETHANOL
• 6-Isoquinolinecarboxaldehyde (9CI)
• ISOQUINOLINE N-OXIDE
• ISOQUINOLINE-1-CARBALDEHYDE
• 8-Isoquinolinecarbonitrile(9CI)
• ISOQUINOLINE-1-CARBOXYLIC ACID METHYL ESTER
• ETHYL ISOQUINOLINE-3-CARBOXYLATE
• Isoquinoline-3-carboxylic acid
• ISOQUINOLINE-5-CARBOXYLIC ACID
• 7-Isoquinolinecarboxaldehyde (6CI,9CI)
• p-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolyl)ethyl]benzenesulphonamide
• 7-isoquinolinecarboxylic acid
• ISOQUINOLINE-5-CARBALDEHYDE
• QUINOLINE-4-CARBOXYLIC ACID HYDRAZIDE