2-Bromoethanol → 3-Amino-4-chloro-5-((2-hydroxyethyl)amino)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-diamino-4-chlorobenzonitrile (200 mg, 1.193 mmol) in DMF (2 mL) was added Hunig's base (2.501 mL, 14.32 mmol) followed by 2-bromoethanol (0.506 mL, 7.16 mmol). The resulting solution was heated at 100° C. for 10 h. LC-MS indicated ca. 30% conversion. It was passed through a pad of celite, rinsed with EtOAc. After concentration, purification via silica gel chromatography (0-70% EtOAc in Hexanes, 24 g) gave 3-amino-4-chloro-5-((2-hydroxyethyl)amino)benzonitrile (75 mg) as an orange oil.

Provenance & Evidence