Ammonia → 4-Aminoisoquinoline

Temperature

165 °C

A suspension of 4-bromoisoquinoline (25.0 g), copper(II) sulfate pentahydrate (30.4 g, Nacalai Tesque), 28% aqueous ammonia (100 ml) and 1,4-dioxane (100 ml) was stirred in a sealed tube at 165° C. for 21 hours. The reaction mixture was cooled to room temperature, the insoluble matters were removed by filtration through Celite, and the filtrate was 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 (chloroform:methanol=9:1) to obtain the title compound (13.2 g).

1. temperatureThe reaction mixture was cooled to room temperature
2. customthe insoluble matters were removed by filtration through Celite
3. extractionthe filtrate was extracted twice with ethyl acetate (150 ml for each time)
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=9:1)

ORD record

ord-5ea2cb1dd9a846b5bf3301835d03cccb

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07094789B2