Triethylamine → N,3-dihydroxybenzenecarboximidamide

Participants

Reaction Steps

To a suspension of 15.84 g (0.228 mol) of hydroxylamine hydrochloride in 75 ml of DMSO there are added 32 ml (0.228 mol) of triethylamine. The solution is stirred vigorously for 30 minutes and is then diluted with a small amount of THF. After stirring for 10 minutes, the triethylamine hydrochloride is filtered off and the residue is rinsed with THF. After the filtrate has been concentrated (evaporating off the THF), 10 g (83.9 mmol) of 3-hydroxybenzonitrile are added to the solution obtained. The solution is stirred at ambient temperature for 16 hours. After diluting with cold water, the mixture is extracted 3 times with ethyl acetate and the organic phase is washed with brine. The expected product is obtained after drying over MgSO4 and evaporation.

Provenance & Evidence