Aniline → 4-Chloronaphthylamine

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The following intermediate anilines and aromatic amines were prepared in a manner similar to that described in the indicated publication. and were then reacted with the appropriate benzoyl isocyanate according to the procedure employed in Example II above: 5-amino-3-methyl-1,2,4-oxadiazole described in U.S. Pat. No. 3,917,478 (Compound 82); 2-amino-5-(l-naphthyl) methylthio-1,3,4-thiadiazole described in German Patent 1,079.060 (Compound 38); 5-(4-nitrophenyl)-3-trifluoromethyl-1,2,4-oxadiazole described in U.S. Pat. No. 3,917,478 (Compound 50) in which the reduction conditions of Example I, Part B above were used to prepare the corresponding aniline; 1-chloro-4-nitronaphthalene described in Bassilios, Bull. Soc. Chim. Fr., 1951, 651 in which catalytic reduction (Example I. Part B above) afforded 1-amino-4-chloronaphthalene (Compound 40); l-chloro-4-nitronaphthalene was converted into l-amino-4-(2,4-dimethylphenoxy) naphthalene according to U.S. patent application Ser. No. 495,331, filed May 20, 1983 (Compound 42); 9-nitroanthracene was reduced using the procedure described in Example I. Part B above (Compound 44); l-amino-4-chloro-5,6,7,8-tetrahydronaphthalene described in Press and Hoffman, Org. Prep. Proc. Int., 1982. 14,204 and Simonetta Beltrane. Gazz. Chim. Ital., 1958, 88,769 (Compound 70); 3,5-dichloro-4-[4-chloro-l-naphthoxy)butoxy] aniline and 4-[l-(l-naphthyl)ethoxy] aniline described in U.S. patent application Ser. No. 430,368, filed Sep. 30, 1982 (Compounds 66 and 81); 1,1-bis-(4-chlorophenyl)methylamine and alpha-methyl-4-chlorobenzylamine described in Cram and Guthrie, J. Am. Chem. Soc., 1966, 88, 5760 (Compounds 83 and 84): and alpha-amino-4-chlorophenylacetonitrile described in Stevens et al., J. Chem. Soc., 1931, 2568 (Compound 86). Compounds 51 and 52 were prepared from commercially available anilines or amines according to the procedure employed in Example II above.

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