3,5-Dimethoxyaniline → 3-Amino-5-methoxyphenol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-dimethoxyaniline (2.53 g, 16.5 mmol) in N-methylpyrrolidinone (10 ml) was added sodium thiomethoxide (2.32 g, 33.1 mmol). The reaction mixture was heated to 140° C. for 2.5 hours and then stirred at ambient temperature for a further 18 hours. The mixture was poured into a saturated solution of NaH2PO4 (50 ml) and then extracted with ethyl acetate. The combined organic layers were filtered through a hydrophobic frit and the solvent was removed under reduced pressure to give a dark red oil. The crude residue was purified by normal phase chromatography, eluting with iso-hexane and increasing amounts of ethyl acetate to give 3-amino-5-methoxyphenol, as a pale yellow solid (1.53 g).

Provenance & Evidence