ChemicalBook CAS DataBase List 7,8-DIHYDROISOQUINOLIN-5(6H)-ONE

7,8-DIHYDROISOQUINOLIN-5(6H)-ONE synthesis

9synthesis methods

Product Name:7,8-DIHYDROISOQUINOLIN-5(6H)-ONE
CAS Number:21917-86-2
Molecular formula:C9H9NO
Molecular Weight:147.17

5-hydroxy-5,6,7,8-tetrahydroisoquinoline

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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 ): t_R = 2.52 min; m/z = 148.0 [M+H]⁺.