ChemicalBook CAS DataBase List 5-METHOXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE

5-METHOXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE synthesis

7synthesis methods

Product Name:5-METHOXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE
CAS Number:129075-49-6
Molecular formula:C10H11NO2
Molecular Weight:177.2

13336-31-7

5-METHOXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE

129075-49-6

GENERAL METHOD: 4-methoxy-1-indanone (1.5 mmol) was dissolved in 37% hydrochloric acid (5 mL) at 0°C and sodium azide (NaN3, 0.2 g, 3.0 mmol) was added slowly. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was poured into ice water and adjusted to alkaline with sodium carbonate (Na2CO3). The aqueous phase was extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography with the eluent being a solvent mixture of dichloromethane (CH2Cl2) and ethyl acetate (AcOEt) (9:1, v/v).

13336-31-7 Synthesis

13336-31-7
159 suppliers
$5.00/100mg

129075-49-6
47 suppliers
$45.00/10mg

Yield:129075-49-6 42%

Reaction Conditions:

with hydrogenchloride;sodium azide in water at 0 - 20;

Steps:

General procedure for the synthesis of 3,4-dihydroisoquinolin-1(2H)-one derivatives
General procedure: To a solution of the appropriate indan-1-one (1.5 mmol) in 37% HCl (5 mL) at 0 °C NaN₃ (0.2 g, 3.0 mmol) was cautiously added. The mixture was stirred overnight at room temperature. The mixture was poured into ice and made basic with Na₂CO₃. The aqueous layer was extracted with ethyl acetate (3 × 10 mL). The collected organic phases were dried over Na₂SO₄ and concentrated under reduced pressure to give a crude residue which was purified by column chromatography with CH₂Cl₂/AcOEt (9:1) as eluent.

References:

Abate, Carmen;Selivanova, Svetlana V.;Müller, Adrienne;Krämer, Stefanie D.;Schibli, Roger;Marottoli, Roberta;Perrone, Roberto;Berardi, Francesco;Niso, Mauro;Ametamey, Simon M. [European Journal of Medicinal Chemistry,2013,vol. 69,p. 920 - 930] Location in patent:supporting information

FullText