It was found that, when
P-xylyiene dichloride was treated with aqueous methanol saturated with ammonia in the presence of ammonium carbonate,
P-xylylenediamine (
P-XDA) was formed in a good yield. The product
P-XDA was isolated in the form of its N, N'-diacetyl derivative. The diacetyl-
P-XDA was hydrolyzed with hydrochloric acid into
P-XDA hydrochloride, from which the free base was obtained upon treatment with methanolic sodium hydroxide.
In the course of ammonolysis, a large amount of 4-aminomethylbenzylcarbamic acid (AMBC) was precipitated. AMBC was obtainable in a pure state (mp 168173°C) from
P-XDA, and was also readily converted into
P-XDA and its derivatives in a good yield. AMBC is a new intermediate to
P-XDA.
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