1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carbaldehyde synthesis

3synthesis methods

Product Name:1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carbaldehyde
CAS Number:952587-40-5
Molecular formula:C10H9NO2
Molecular Weight:175.18

7-Vinyl-3,4-dihydroisoquinolin-1(2H)-one

952587-39-2
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1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carbaldehyde

952587-40-5
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Yield:952587-40-5 57%

Reaction Conditions:

with sodium periodate;osmium(VIII) oxide;water in 1,4-dioxane at 20; for 0.5 h;

Steps:

16.c

(c) 1 -Oxo-i ,2, 3,4-tetrahydro-7-isoquinolinecarbaldehyde; To a solution of 7-ethenyl-3,4-dihydro-1 (2H)-isoquinolinone (232 mg, 1.341 mmol) in 1 ,4-dioxane (15 ml) and water (3 ml) at O⁰C was added sodium periodate (660mg, 3.08 mmol) and osmium tetroxide (1 .5 ml of a 4% aqueous solution). The reaction mixture was warmed to room temperature and stirred for 0.5h before evaporation of the reaction mixture. The residue was dissolved in 1 ,4-dioxane (50 ml) and evaporated again. The mixture was then dissolved in dichloromethane (100ml), dried with magnesium sulphate and evaporated. Chromatography on silica, eluting with 0-100% ethyl acetate/hexane, gave the product (133 mg, 57%). MS (+ve ion electrospray) m/z 176 (MH+).

References:

WO2007/115947,2007,A1 Location in patent:Page/Page column 56

7-BROMO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE

891782-60-8
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952587-40-5
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References

66491-03-0 Synthesis

7-AMINO-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE

66491-03-0
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References