How do I reduce a cyano group in the presence of an aromatic nitro- and chlorine group?

• Asking a group of chemist how to reduce a cyano group, 99% of the scientist know the answer.
• Asking how to reduce the cyano group in the presence of a nitro group, reduces the number of correct answers to 30%.
• Less than 1% of the scientist have an idea how to reduce the cyano group in the presence of both groups.

Do you know the answer how to reduce the cyano group?

By searching the reaction database you will get your answer.

Search

There was no answer in the databases, the query is too narrowly defined.

Answer

More General Query

Answer

There was one answer in ca. 500'000 reaction! The second answer is interesting, note the yield!

The question was not so simple. The answer is to use "BH3" in suito. I helped you by showing you the proper reactions. It was a little bit more work to find these reactions. The main point is that we found the right conditions in spite of the fact that this reaction was not in the database. In the late 90ties a similar reaction is actually reported in CrossFire Beilstein.