2-Aminopyridine → 3-Chloro-1-methoxyisoquinoline

Participants

Reaction Conditions

Reaction Steps

Into a sealed tube were added 1,3-dichloroisoquinoline (501 mg, 2.45 mmol), 2-aminopyridine (31 mg, 0.33 mmol), cuprous monochloride (37.2 mg, 0.162 mmol), MeONa (824 mg, 5.92 mmol), MeOH (3 ml) and diglyne (8 ml). The tube was sealed, evacuated and filled with N2 three times. The combined mixture was heated at 125° C. for 3 days under an atmosphere of nitrogen. After that time, the mixture was treated with water (20 ml) and extracted with EtOAc (3×50 ml). The organic extracts were washed with water (3×30 ml), brine (30 ml), dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as light-yellow solid. 1H NMR (400 MHz, CDCl3): δ=4.15 (s, 3H), 7.26 (d, J=0.6 Hz, 1H), 7.51 (ddd, J=3.6, 4.6, 8.2 Hz, 1H), 7.64-7.69 (m, 2H), 8.20 (dd, J=8.4, 1.2 Hz, 1H). MS(ES+): m/z=194.08/196.01 (80/28) [MH+]. HPLC: tR=4.00 min (polar—5 min, ZQ3).

Provenance & Evidence