ChemicalBook CAS DataBase List ISOQUINOLINE-1-CARBALDEHYDE

ISOQUINOLINE-1-CARBALDEHYDE synthesis

11synthesis methods

Product Name:ISOQUINOLINE-1-CARBALDEHYDE
CAS Number:4494-18-2
Molecular formula:C10H7NO
Molecular Weight:157.17

1721-93-3
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4494-18-2
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Yield: 77%

Reaction Conditions:

with selenium(IV) oxide in 1,4-dioxane;hexane;ethyl acetate

Steps:

102.1 (Step 1)
(Step 1) Synthesis of 1-isoquinolinecarbaldehyde In 1,4-dioxane (20 ml) was dissolved 1-methylisoquinoline (300 mg, 2.10 mmol). To the resulting solution was added selenium dioxide (323 mg, 2.91 mmol), followed by heating under reflux for 1.5 hours under a nitrogen gas stream. After cooling to room temperature, the reaction mixture was filtered through Celite. The filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (5:1, v/v) eluate fractions, 1-isoquinolinecarbaldehyde (252 mg, 77%) was obtained as a white solid. ¹H-NMR (CDCl₃) δ: 7.73-7.79 (m, 2H), 7.88-7.93 (m, 2H), 8.74-8.76 (m, 1H), 9.30-9.33 (m, 1H), 10.39 (s, 1H). MS (ESI) m/z 158 (M⁺+1).

References:

DAIICHI PHARMACEUTICAL CO., LTD. EP1346982, 2003, A1