1-AMinoisoquinoline-4-carbonitrile synthesis

Yield:53000-57-0 81.6%

Reaction Conditions:

with sodium methylate in methanol at 20; for 1 h;Inert atmosphere;

Steps:

1-aminoisoquinoline-4-carbonitrile (27)

To a solution of 2-cyanophenylacetonitrile 26 (300mg, 2.11mmol) and 1, 3, 5-triazine (205.3mg, 2.53mmol) in MeOH (10.6mL) was added 28% NaOMe methanol solution (2.04g, 10.6mmol). The mixture was stirred at ambient temperature for 1h. The reaction mixture was poured into with 10% NH₄Cl solution and MeOH. After removing the solvent, EtOAc and H₂O was added. After separating EtOAc, the aqueous phase was extracted with EtOAc twice. The combined organics were dried over MgSO₄, filtered, and concentrated in vacuo. The crude product was stirred in iPrOH/Heptane. The solid was collected after filtration to give the known amino-isoquinoline 27 (319.1mg, 81.6%) as pale yellow solid. The product was identified with previously reported data.

References:

Hayashida, Joji;Yoshida, Shinya [Tetrahedron Letters,2018,vol. 59,# 43,p. 3876 - 3879] Location in patent:supporting information