ISOQUINOLINE-1-CARBALDEHYDE

Yellow solid

(Step 1) To a stirred solution of 1-methylisoquinoline (12g) (300 mg, 2.10 mmol) in dioxane (20 ml) was added SeOSeO2 (757 mg, 6.82 mmol) and 1-methylisoquinoline (698 mg, 4.87 mmol) were dissolved in dioxane (10 mL) and the mixture was stirred at reflux for 16 h, cooled and filtered. The filtrate was concentrated and the residue was column chromatographed. The compound was a white solid (485 mg, yield 63percent).(b) A solution of methyl 1-isoquinolinecarboxylate (1.00 g, 5.34 mmol) in dry THF (30 mL) was cooled to -70 °C in a dry ice/MeOH bath. To that solution was added a suspension of LiAlHGeneral procedure: Heterocycle (0.10mmol, 1equiv)ammonium persulfate (0.30 mmol, 3 equiv), Cs2CO3(0.20mmol, 2 equiv)were placed in a dry glass tube.Then, anhydrous DMSO1 mL) and2, 2-diethoxyacetic acid (0.7mmol7equiv), wereinjected into the tube by syringe under a N2atmosphere.The solution was then stirred at roomtemperature under the irradiation of 15W blueLEDs strip for 24h.After completion of the reaction, the mixture was quenched by addition of1.2mL of 3.0 M HCl, stirred for 20hthen saturated Na2CO3solution was added to adjust pH tobasicextract with CH2Cl2, the combined organic layers was washed with brine, then dry overanhydrous Na2SO4. The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum and ethylacetate.

Molecular Weight:157.17
XLogP3:2
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