Hydrochloric Acid → 6-Methoxy-isoquinoline 2-oxide hydrochloride

Participants

Reaction Steps

At room temperature 133 g of m-chloroperbenzoic acid (purity 75%) was added in portions to a stirred solution of 6-methoxy-isoquinoline [Hendrickson, J. B.; Rodriguez, C.; J. Org. Chem. 1983, 48, 3344-3346; 79.8 g; 500 mmol] in 1.2 L of dichloromethane. Stirring was continued for 3 hours and subsequently methanol (1 L) was added. The bulk was reduced to 700 mL after which 800 mL of a saturated solution of hydrogen chloride in diethyl ether was added. Dilution with 1.5 L of diethyl ether resulted in precipitation of yellow crystals, which were separated by filtration, washed with chilled diethyl ether and dried in vacuo. Yield: 85 g (80%); white solid; m.p. 189-191° C.; (+)-FAB-MS: 176 (MH+-HCl).

Provenance & Evidence