ChemicalBook CAS DataBase List 7-Methoxy-isoquinolin-1(2H)-one

7-Methoxy-isoquinolin-1(2H)-one synthesis

9synthesis methods

Product Name:7-Methoxy-isoquinolin-1(2H)-one
CAS Number:16027-16-0
Molecular formula:C10H9NO2
Molecular Weight:175.18

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Yield: 78%

Reaction Conditions:

with sodium acetate;bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate in water;1,2-dichloro-ethane at 85; for 16 h;

Steps:

1 7-Methoxyisoquinolin-1(2H)-one (IIi)
To a suspension of 4.4 g (25.1 mmol, 1.0 eq.) of 7-methoxyisoquinoline 2-oxide in 40 mL of 1,2-dichloroethane was added 6.1 g (75.4 mmol, 2.0 eq.) of sodium acetate followed by 23.4 g (50.3 mmol, 2.0 eq.) of bromotripyrrolidinophosphonium hexafluorophosphate and 5 mL of water and the mixture was heated at 85 °C for 16 h. The mixture was allowed to cool to room temperature and the solvent was removed in vacuo. The residue resuspended in 50 mL of water and extracted with 3 x 50 mL of methylene chloride. The combined organic extracts were washed with 80 mL of brine, dried (Na₂SO₄), filtered and the solvent was removed in vacuo. The residue was triturated with 50 mL of methyl tert-butyl ether to provide 2.0 g (11.4 mmol, 78%) of 7-methoxyisoquinolin-1(2H)-one (IIi). LCMS: m/z found 176.1 [M+H]⁺, RT = 1.78 min; ¹H NMR (300 MHz, DMSO-d₆) d 11.19 (bs, 1H), 7.59-7.62 (m, 2H), 7.30-7.33 (m, 1H), 7.04 (t, 1H), 6.51 (d, 1H), 3.85 (s, 3H).

References:

ARBUTUS BIOPHARMA CORPORATION;ARBUTUS BIOPHARMA, INC.;COLE, Andrew G.;FAN, Yi;KULTGEN, Steven;MESAROS, Eugen WO2020/123674, 2020, A1 Location in patent:Page/Page column 292