During the development of a sodium borohydride mediated reductive amination of 3-nitrobenzaldehyde with methylamine, studies revealed that partial reduction of the nitro group occurred, and potentially dangerous azo- and azoxy-containing products were generated. Borane-tert-butylamine activated with methanesulfonic acid was determined to be a safer reducing agent, and abuse tests on the reduction stage of the process have demonstrated that partial reduction of the nitro group did not occur. Conditions were developed that were suitable for scale-up to a pilot plant.

中文翻译：

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评估甲基（3-硝基苄基）胺盐酸盐的还原胺化路线

在硼氢化钠介导的3-硝基苯甲醛与甲胺的还原胺化反应过程中，研究表明硝基发生部分还原，并生成了潜在的危险的含偶氮和乙氧基的产物。经甲磺酸活化的硼烷叔丁胺被确定为较安全的还原剂，在该方法的还原阶段进行的滥用试验表明，不会发生硝基的部分还原。开发了适合扩大到中试工厂的条件。