ChemicalBook CAS DataBase List 2-(4-Hydroxyphenyl)-2H-isoquinolin-1-one

2-(4-Hydroxyphenyl)-2H-isoquinolin-1-one synthesis

3synthesis methods

Product Name:2-(4-Hydroxyphenyl)-2H-isoquinolin-1-one
CAS Number:20434-92-8
Molecular formula:C15H11NO2
Molecular Weight:237.25

1(2H)-Isoquinolinone, 3-(4-methoxyphenyl)-

13670-91-2
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2-(4-Hydroxyphenyl)-2H-isoquinolin-1-one

20434-92-8
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Yield:20434-92-8 84%

Reaction Conditions:

with pyridine hydrochloride at 190; for 2 h;

Steps:

21

To a solution of n-methyl-o-toluamide (2.0 g, 13.4 mmol) in THF (30 ml_), n-butyl lithium (12.3 mL, 30.8 mmol, 2.5 M solution in hexane) was EPO added slowly under nitrogen with cooling (ice-salt bath) maintaining the temperature below 20⁰C. After addition, the mixture was stirred for 1 h at O⁰C₁ then cooled to -50⁰C. A solution of 4-methoxy benzonitrile (2.14 g, 16.08 mmol) in THF (5 mL) was added quickly. The cooling bath was removed and the reaction was allowed to warm to room temperature. A saturated aqueous NH₄CI solution was added during cooling, and the solid was isolated by filtration to give the methoxy compound (2.2 g, 65%). The methoxy compound (750 mg, 2.98 mmol) was dissolved in a 50 mL flask and pyridinium hydrochloride (10 g) was added. The mixture was heated at 190⁰C for 2 h, then cooled to room temperature . The reaction was then diluted with water, neutralized with NaHCO₃ and the solid was isolated by filtration to give 600 mg of 3-(4-hydroxyphenyl)-2H-isoquinolin-1-one (84%). MS (ES) m/z: 238.92 (M+1), 237.89 (M); MP 239-241⁰C.

References:

WO2007/16525,2007,A2 Location in patent:Page/Page column 68-69

2170-09-4 Synthesis

2170-09-4
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References

874-90-8 Synthesis

874-90-8
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$8.00/10g

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References