I am currently trying to achieve the reduction of cyano group into primary amines. A brief review of literatures indicate that H2 /Pd/C or H2 /Raney Ni was most used, however usually with extra pressure. Alternatively NaBH4/NiCl2 or NaBH4/CoCl2 would obtain product in lab scale conveniently.

However as observed in many cases with different substrates, Non-N-containing substrates would smoothly convert but N-containing substrates would either give a mixture or didn't react at all.

Would someone experienced in this field kindly explain this and suggest me some other ways to do the reduction?

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N-containing rings examples: Pyridines/ pyrazines / benzimidazoles