REDUCTION WITH ALKALINE FORMALDEHYDE 283 aniline (80% yield), o-ethoxyaniline (75% yield), and 4-amino-4'-methyldiphenyl ether (50% yield) are indicative of the possibilities. Alkaline formaldehyde and hypophosphorous acid are about equally valuable in deaminating such compounds^ ethanol is not satisfactory here. , Alkaline formaldehyde is also useful in removing the amino group of ortho-and paro-chloroanilines; 50-55% yields of chlorobenzene are obtained. With 2,5-dichloroaniline, however, the yield falls to 10%. The formaldehyde procedure cannot be applied to nitroamines inasmuch as reduction of the nitro group occurs. Only a 20% yield of nitrobenzene is obtained from o-nitroaniline, and with the meta and para isomers the yield drops to 10%.* There is a substantial group of diazonium salts to which the alkaline formaldehyde method, or any other deamination process requiring alka-line conditions, should not be applied, inasmuch as they are unstable in the presence of alkali. This instability is merely an extension of the
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