Sodium Hydroxide → HCID 70388848, compound

Participants

Reaction Conditions

Reaction Steps

A mechanically stirred suspension of 2-(2-benzyloxyethyl)-3-fluoroaniline hydrochloride (53 g, 0.188 mole) in a mixture of water (30 mL), concentrated HCl (127 mL) and glacial HOAc (127 mL) was cooled to -10° C. (internal temperature). A solution of NaNO2 (14.27 g, 0.206 mole) in water (52 mL) was added dropwise while maintaining the internal temperature at -10° C. The resulting red solution was stirred an additional 75 minutes at -10° C. and then treated dropwise (over 30 minutes) with a solution of tin (II) chloride dihydrate (84.8 g, 0.376 mole) in concentrated HCl (97 mL) precooled to -40° C. The mixture was stirred an additional 75 minutes at -10° C. and then cooled at -15° C. and basified (to pH 14) with 50% NaOH (about 320 mL). The internal temperature was kept at - 8°/-10° C. during the addition of the base. The mixture was extracted with ether (3×). The combined extracts were washed with brine, dried (anhydrous K2CO3) and carefully acidified with ethereal HCl. Removal of the solvent provided the title compound as a tan solid (54 g, 96.9%). Trituration with light petroleum ether removed the less polar impurities and provided pure product (48.4 g, 86.8%).

Provenance & Evidence