Water → 5-Amino-1-chloroisoquinoline

Participants

Reaction Steps

Copper (II) acetylacetonate (253 mg) was suspended in ethanol (10 ml) and sodium borohydride (366 mg) was added in one portion. The mixture was stirred for 5 minutes, by which time a black suspension had appeared. A suspension of 1-chloro-5-nitroisoquinoline (Description 47; 1.01 g, 4.84 mmol) in ethanol (20 ml) was then added over 15 minutes whilst cooling in a water bath; the mixture effervesced. The mixture was stirred at room temperature for 1 hour, then more sodium borohydride (160 mg) was added and stirring continued for a further 1 hour. Water (100 ml) was added then the ethanol was evaporated and the mixture extracted with ethyl acetate (3×50 ml). The combined organic layers were dried (Na2SO4) and evaporated. Purification of the residue by flash column chromatography using 5% methanol-dichloromethane as eluant gave the title compound (210 mg).

Provenance & Evidence