2-Methyl-4-nitroaniline → N-allyl-2-methyl-4-nitroaniline

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Reaction Steps

The particularly advantageous compound I-8 according to the invention can be prepared, for example, by formylating 2-methyl-4-nitroaniline using 95% strength formic acid, alkylating the resultant N-formyl-2-methyl-4-nitroaniline using allyl chloride under phase-transfer conditions and reducing the resultant N-allyl-N-formyl-2-methyl-4-nitroaniline. On the other hand, it is also possible to hydrolyze the intermediate N-allyl-N-formyl-2-methyl-4-nitroaniline to form N-allyl-2-methyl-4-nitroaniline, and to alkylate the latter using methyliodide to give the compound I-8 according to the invention. To this end, the intermediate N-allyl-2-methyl-4-nitroaniline can also be prepared by alkylating N-formyl-2-methyl-4-nitroaniline using allyl chloride. In addition, it is also possible to reduce the intermediate N-formyl-2-methyl-4-nitroaniline using a boron hydride in tetrahydrofuran to give the corresponding N-methyl derivative, which is subsequently alkylated using allyl chloride to give the compound I-8 according to the invention.

Provenance & Evidence