N-Phenylglycine → Glycine, N-nitroso-N-phenyl-

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Reaction Steps

The precursor N-nitrosophenylglycine was prepared according to the method described in Organic Syntheses, Coll. Vol. 5, p. 962 (1973); Vol. 45, p. 96 (1965). N-phenyl glycine (50 g) was dissolved in water (600 ml) with stirring, and the solution was cooled to below 0° C. in a salt/ice bath mixture. To this was slowly added a cooled solution of sodium nitrite (25 g) in water (150 ml) so that the temperature of the mixture never rose above 0° C. After addition was complete, the mixture was stirred below 0° C. for 40 minutes after which a red-brown solution was obtained with a small amount of brown solid residue. The residue was removed by filtering the solution under vacuum, and the clear liquid was decolorised by treating with charcoal (5 g) for 5 minutes. After filtering off the charcoal, the solution was cooled again and acidified with concentrated hydrochloric acid (50 ml), whereupon a slightly reddish-brown precipitate formed. The mixture was stirred for 10 minutes and then the precipitate was filtered off. This was allowed to dry in air to give a tan coloured powder (48 g).

Provenance & Evidence