ChemicalBook CAS DataBase List ISOQUINOLINE-5-CARBALDEHYDE

ISOQUINOLINE-5-CARBALDEHYDE synthesis

6synthesis methods

Product Name:ISOQUINOLINE-5-CARBALDEHYDE
CAS Number:80278-67-7
Molecular formula:C10H7NO
Molecular Weight:157.17

1532-71-4 Synthesis

1532-71-4
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$9.00/100mg

80278-67-7
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$25.00/250mg

Yield:-

Reaction Conditions:

with n-butyllithium;ammonium chloride in tetrahydrofuran;ethanol;N,N-dimethyl-formamide

Steps:

2 5-Isoquinolinecarboxaldehyde
EXAMPLE 2 5-Isoquinolinecarboxaldehyde To a solution of n-butyllithium (19.3 mL of 2.5M 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 (199), 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 minute. 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, 64% yield) was obtained from chromatography (SiO₂ Type-H, 50% EtOAc in hexanes) and recrystallization (ethanol): mp 114-116° C.;

References:

Purdue Research Foundation US6645975, 2003, B1