Aniline → HCID 10822558, compound

Participants

Reaction Steps

A solution of 2-fluoro-4-hydroxyaniline hydrochloride (3 g) in MeOH (50 mL) was treated with aqueous NaOH (0.74 g in 10 mL deionized water) and the resulting clear solution was concentrated to dryness to provide a residue of crude aniline free base. A 0° C. solution of the crude aniline residue in 1:1 AcOH/deionized water (32 mL) in a pressure tube was treated with liquid ethylene oxide condensed at −78° C. (7.8 g), the tube was sealed, and the reaction mixture allowed to warm up to RT. The reaction mixture was stirred at RT 48 h then cooled, evaporated to dryness and purified by silica gel chromatography (0-7% MeOH/DCM) to provide N,N-bis-(2-hydroxyethyl)-2-fluoro-4-hydroxyaniline (2 g) as a grey powder.

Provenance & Evidence