7,8-DIHYDROISOQUINOLIN-5(6H)-ONE synthesis
- Product Name:7,8-DIHYDROISOQUINOLIN-5(6H)-ONE
- CAS Number:21917-86-2
- Molecular formula:C9H9NO
- Molecular Weight:147.17
97112-03-3
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21917-86-2
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Yield: 89%
Reaction Conditions:
Stage #1:5-hydroxy-5,6,7,8-tetrahydroisoquinoline with oxalyl dichloride;dimethyl sulfoxide in dichloromethane at -60 - -50; for 0.333333 h;
Stage #2: with triethylamine in dichloromethane at -60 - 20; for 0.0833333 h;
Steps:
3
REFERENCE EXAMPLE 3; 7,8-Dihydro-6/-/-isoquinolin-5-one; To a solution of oxalyl chloride (1.9 ml_, 22 mmol) in CH2CI2 (80 ml_) under argon and previously cooled at -50/-600C, a solution of DMSO (3.1 ml_, 44 mmol) in CH2CI2 (10 imL) was added. It was stirred for 5 min at -50/-600C and a solution of 5,6,7,8-tetrahydroisoquinolin-5-ol (3.00 g, 20 mmol, obtained in reference example 2) in CH2CI2 (20 ml_) was added. After stirring for 15 min at -50/-600C, TEA (13.9 mL, 100 mmol) was added. It was stirred for 5 min at -50/-600C and allowed to warm to room temperature. It was poured over a mixture of water-ice. It was extracted 3 times with CH2CI2. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 2.63 g of the desired compound as an orange liquid (yield: 89%).LC-MS (method 1 ): tR = 2.52 min; m/z = 148.0 [M+H]+.
References:
PALAU PHARMA, S. A. WO2007/60198, 2007, A1 Location in patent:Page/Page column 33
36556-06-6
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21917-86-2
91 suppliers
$274.00/250mg
36556-06-6
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21917-88-4
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21917-86-2
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103441-65-2
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21917-86-2
91 suppliers
$274.00/250mg
36556-06-6
133 suppliers
$45.00/250mg
21917-86-2
91 suppliers
$274.00/250mg
135311-97-6
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