Amide reduction is a reaction in organic synthesis where an amide is reduced to either an amine or an aldehyde functional group.
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Catalytic Hydrogenation
Catalytic hydrogenation can be used to reduce amides to amines; however, the process often requires high hydrogenation pressures and reaction temperatures to be effective (i.e. often requiring pressures above 197 atm and temperatures exceeding 200 °C). Selective catalysts for the reaction include Copper chromite, Rhenium trioxide, and Rhenium(VII) oxide.
Non-catalytic routes to amines
Reducing agents able to affect this reaction include metal hydrides such as lithium aluminium hydride, or lithium borohydride in mixed solvents of tetrahydrofuran and methanol,
Non-catalytic routes to aldehydes
N,N-disubstituted amides can be reduced to aldehydes by using an excess of the amide:
R(CO)NRR' + LiAlH4 → RCHO + HNRR'With further reduction the alcohol is obtained.
Some amides can be reduced to aldehydes in the Sonn-Müller method.
Hydrosilylation
A well known method for amide reduction is hydrosilylation with silyl hydrides and a suitable catalyst based on Rh, Ru, Pt, Pd, Ir, Os, Re, Mn, Mo, In, or Ti.
Iron catalysis by triiron dodecacarbonyl in combination with polymethylhydrosiloxane has been reported.