One other way for diazepam synthesis has been suggested, which is derived from 1-methyl-3-phenyl-5-chloro-2-aminomethylindole (5.1.12), the oxidation of which by chromium(VI) oxide gives diazepam. The synthesis begins with 5-chloroaniline, which upon interaction with nitrous acid gives a diazonium salt (5.1.7). Azocoupling of this product with ethyl a-benzylacetoacetic ester in an alkaline solution gives the 4-chlorophenyl-hydrazone of the ethyl ester of phenylpyruvic acid (5.1.8), which in the presence of hydrochloric acid undergoes a Fischer indole synthesis reaction and transforms into the ethyl ester of 5-chloro-3-phenylindolyl-2-carboxylic acid (5.1.9). Alkylation of the resulting indole at the nitrogen atom using dimethylsulfate gives 1-methyl-5-chloro-3-phenyl-indolyl-2-carboxylic acid ethyl ester (5.1.10). The reaction of the resulting product with ammonia gives the respective amide (5.1.11), which is reduced by lithium aluminum
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