Reaktion #42541

Reaktionsgleichung

dry ice

7-bromo-N-butyl-N-methylisoquinolin-1-amine

sec-butyllithium

hydrochloric acid

→

1-[butyl(methyl)amino]isoquinoline-7-carboxylic acid

Lösungsmittel

—

cyclohexanes

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   EinengenThe aqueous phase was concentrated under reduced pressure
4. 4
   Sonstigeto yield a yellow oil
5. 5
   SonstigePurification by flash column chromatography (silica, 50:30:15:5 ethyl acetate/chloroform/methanol/ammonium hydroxide)

Vorschrift

To a −60° C. solution of 7-bromo-N-butyl-N-methylisoquinolin-1-amine (230 mg, 0.78 mmol) in diethyl ether was added sec-butyllithium (1.00 mL of a 1.3 M solution in cyclohexanes, 1.30 mmol). The solution was stirred at −60° C. for 20 min then excess dry ice (CO2) was added and the reaction mixture was allowed to warm to room temperature. The reaction mixture was then acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The aqueous phase was concentrated under reduced pressure to yield a yellow oil. Purification by flash column chromatography (silica, 50:30:15:5 ethyl acetate/chloroform/methanol/ammonium hydroxide) provided 1-[butyl(methyl)amino]isoquinoline-7-carboxylic acid (90 mg): ESI MS m/z 259 [M+H]+.

Quelle