1,6-Dibromo-3-isoquinolinamine

925672-88-4

925672-85-1

The general procedure for the synthesis of 1,6-dibromoisoquinolin-3-amine from 5-bromo-2-cyanophenylacetonitrile was as follows: 4-bromo-2-(cyanomethyl)benzonitrile (75 g, 339 mmol) was dissolved in 2,2-dichloroacetic acid (150 mL, 339 mmol). The reaction mixture was cooled to 0°C in an ice water bath. HBr gas (27.5 g, 339 mmol) was passed into the cooled solution until a yellow precipitate was observed to precipitate and form a yellow slurry. The passage of HBr gas was continued for 5 min. Subsequently, the reaction mixture was slowly warmed up to room temperature over a period of 1 hour. The slurry was again cooled to 0 °C in an ice water bath and ether (200 mL) was added. The mixture was stirred at 5 °C for 20 min. The yellow solid product was collected by filtration to give 1,6-dibromoisoquinolin-3-amine (42 g, 41% yield). lcms (API-ES) m/z: 303 (M + H+).