Hydrochloric Acid → 3'-Amino-4'-methoxyacetanilide

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Other aqueous processes of acylation have been taught to yield the single desired isomer compound I where R is --CH3 and --XR1 is --COCH3, but at lower yield. German 1,543,625, Example 1, teaches the acylation of freshly-distilled 2,4-diaminoanisole with acetic anhydride in water solution, without the addition of hydrochloric acid, to give 3-amino-4-methoxyacetanilide in 75% yield before recrystallization. Publication, Board of Federal Intelligence Agency, P.B. 74 051, p. 33 teaches a similar conversion of 2,4-diaminoanisole to 2-amino-4-acetamidoanisole, in aqueous solution, with acetic anhydride, in the presence of magnesia at 65% yield.

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