| 摘要 |
1,153,796. Substituted benzamides. SOC. D'ETUDES SCIENTIFIQUES ET INDUSTRIELLES DE L'ILE-DE-FRANCE. 11 Nov., 1966 [27 Dec., 1965], No. 50701/66. Heading C2C. A substituted benzamide of general formula in which A is hydrogen, a C 1 -C 5 alkyl group or a C 2 -C 5 alkenyl group; X is amino, alkylamino, dialkylamino or acylamino radical; Y is a halogen atom; and n is 1, 2 or 3 and in which one of the -CH 2 - groups in A or the carboxamide group may be branched to form the group in which R 3 is a radical containing 1-4 carbon atoms and in which R 1 and R 2 are identical or different C 1 -C 5 alkyl groups or together with the nitrogen atom to which they are attached form a heterocyclic ring, may be prepared by nitrating a p-halogeno-phenol to form the 2-nitro-4-halo-phenol; optionally alkylating or alkenylating thio to form a 2-nitro-4-haloalkoxy or alkenyloxy benzene; reducing the 2- nitro - 4 - halo - phenol or alkoxy or alkenoxy phenol to the corresponding amino compound, acylating the amino compound to form the 2- acetylamino - 4 - halo - phenol, alkoxyphenol or alkenyloxyphenol; nitrating the 2-acetylamino compound to form the corresponding 2-acetylamino - 4 - halo - 5 - nitro compound; hydrolysing this to form the 2-amino compound; diazotizing this compound and treating the product with cuprous cyanide to form the corresponding 2-cyano compound; hydrolysing the cyano compound and heating with an alcohol to get the corresponding alkyl ester; heating this with an asymmetrically disubstituted diamine to get the corresponding N-(tertiary amino alkyl)-benzamide and reducing and optionally alkylating or acylating the nitro group. An example is given of the preparation of N - (diethyl aminoethyl) - 2 - methoxy - 4- amino-5-chlorobenzamide and its conversion to its hydrochloride.
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