Réaction #10644

Équation de réaction

hydrochloric acid

Intermediate 87

4-aminoisoquinoline

hydrochloric acid

sodium nitrite

ammonia

→

title compound

4-chloroisoquinoline

Conditions de réaction

Traitement

1. 1
   Extractionextracted twice with ethyl acetate (150 ml for each time)
2. 2
   SéchageThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Autrethe solvent was evaporated under reduced pressure
4. 4
   AutreThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Mode opératoire

Intermediate 87 (1.27 g) was dissolved in 1 N aqueous hydrochloric acid (36 ml) and added dropwise with an aqueous solution (36 ml) of sodium nitrite (1.21 g, Wako Pure Chemical Industries) with ice cooling. The obtained suspension was added dropwise to a solution of copper(I) chloride (1.83 g, Wako Pure Chemical Industries) in 1 N aqueous hydrochloric acid (20 ml) with ice cooling, then warmed to room temperature and stirred for 15 hours. The reaction mixture was added with 28% aqueous ammonia (50 ml) and extracted twice with ethyl acetate (150 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (433 mg).

Source