ISOQUINOLINE-5-CARBALDEHYDE

Yellow to light brown powder

To a solution of n-butyllithium (19.3 mL of 2.5 M in hexanes, 48 mmol) in a mixture of ether (80 mL) and THF (80 mL) at -78° C. was added dropwise a solution of bromoisoquinoline (5.0 g, 24 mmol) in THF (10 mL). The reaction mixture was stirred at -78° C. under argon for 30 minutes. Following the general procedures described by Pearson, et al., in J. Heterocycl. Chem., Vol. 6 (2), pp. 243-245 (1969), a solution of DMF (3.30 g, 45 mmol) in THF (10 mL) was cooled to -78° C. and quickly added to the isoquinolyllithium solution. The mixture was stirred at -78° C. for 15 minutes. Ethanol (20 mL) was added followed by saturated NH5-Isoquinolinecarboxaldehyde. To a solution of n-butyllithium (19.3 niL of 2.5 M in hexanes, 48 mmol) in a mixture of ether (80 mL) and THF (80 mL) at -780C was added dropwise a solution of bromoisoquinoline (5.0 g, 24 mmol) in THF (10 mL). The reaction mixture was stirred at -780C under argon for 30 minutes. Following the general procedures described by Pearson, et al., in J. Heterocycl. Chem., Vol. 6 (2), pp. 243-245 (1969), a solution of DMF (3.30 g, 45 mmol) in THF (10 mL) was cooled to -780C and quickly added to the isoquinolyllithium solution. The mixture was stirred at -780C for 15 minutes. Ethanol (20 mL) was added followed by saturated NH4Cl solution. The resulting suspension was warmed to room temperature. The organic layer, combined with the ether extraction layer, was dried over Na2SO4. A pale yellow solid (2.4 g, 15 mmol, 64percent yield) was obtained from chromatography (SiO2 Type-H, 50percent EtOAc in hexanes) and recrystallization (ethanol)To a solution of n-butyllithium (19.3 mL of 2.5 M in hexanes, 48 mmol) in a mixture of ether (80 mL) and THF (80 mL) at -78° C. was added dropwise a solution of bromoisoquinoline (5.0 g, 24 mmol) in THF (10 mL). The reaction mixture was stirred at -78° C. under argon for 30 minutes. Following the general procedures described by Pearson, et al., in J. Heterocycl. Chem., Vol. 6 (2), pp. 243-245 (1969), a solution of DMF (3.30 g, 45 mmol) in THF (10 mL) was cooled to -78° C. and quickly added to the isoquinolyllithium solution. The mixture was stirred at -78° C. for 15 minutes. Ethanol (20 mL) was added followed by saturated NH4Cl solution. The resulting suspension was warmed to room temperature. The organic layer, combined with the ether extraction layer, was dried over Na2SO4. A pale yellow solid (2.4 g, 15 mmol, 64percent yield) was obtained from chromatography (SiO2 Type-H, 50percent EtOAc in hexanes) and recrystallization (ethanol): mp 114-116° C.; 1H NMR (DMSO-d6) delta 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) delta 194.23, 153.5, 146.2, 140.2, 135.2, 132.6, 130.2, 128.6, 127.5, and 117.2. Anal. Calcd. for C10H7NO.0.05H2O: C, 75.99; H, 4.53; N, 8.86. Found: C, 75.98, H, 4.66; N, 8.68.

Treatment with cyanoethylphosphonate followed by reduction of samarium (II) iodide can directly convert heteroaryl-formaldehyde to acetonitrile.

Molecular Weight:157.17
XLogP3:1.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:157.052763847
Monoisotopic Mass:157.052763847
Topological Polar Surface Area:30
Heavy Atom Count:12
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes