6-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE Chemical Properties

Melting point:

136-138℃

Boiling point:

439.8±45.0 °C(Predicted)

Density 

1.159

storage temp. 

Sealed in dry,Room Temperature

pka

14.77±0.20(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C10H11NO2/c1-13-8-2-3-9-7(6-8)4-5-11-10(9)12/h2-3,6H,4-5H2,1H3,(H,11,12)

InChIKey

WLQWIZAWNPYMBR-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=C(OC)C=C2)CCN1

Safety Information

HS Code 

2933499090

6-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE Usage And Synthesis

Synthesis

General procedure for the synthesis of 6-(methoxy)-3,4-dihydro-1(2H)-isoquinolinone from the compound (CAS:110192-21-7): the feedstock compound (35.0 g, 167.26 mmol) was slowly added to preheated polyphosphoric acid (184 mL, 183.99 mmol) at 120 °C, keeping the temperature at 120 °C. The reaction mixture was stirred at room temperature for 6 h. Subsequently, the reaction was quenched with ice water, alkalized with K2CO3 to pH neutral and extracted with dichloromethane (DCM). The organic layers were combined, dried with anhydrous Na2SO4, filtered and the solvent concentrated. The crude product was purified by silica gel column chromatography using ethyl acetate (EtOAc)/hexane (1:1) as eluent to afford the target product 6-(methoxy)-3,4-dihydro-1(2H)-isoquinolone (38.5 g, 218 mmol, 76% yield) as a white solid.1H NMR (500 MHz, CDCl3) δ 8.01 (d, J = 8.7 Hz, 1H), 6.90 (d, J = 8.7 Hz, 1H), 6.86 (dd, J = 8.7, 2.4 Hz, 1H), 6.71 (d, J = 2.4 Hz, 1H), 3.85 (s, 3H), 3.56 (td, J = 6.6, 2.8 Hz, 2H), 2.96 (t, J = 6.6 Hz, 2H); EI/ MS m/z 177.1 [M+].

References

[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 207 - 219
[2] Patent: US2017/145007, 2017, A1. Location in patent: Paragraph 0322-0325
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 789 - 801
[4] Patent: WO2012/97682, 2012, A1. Location in patent: Page/Page column 134
[5] Patent: WO2012/97684, 2012, A1. Location in patent: Page/Page column 108

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