Sodium metal and alcohol reduction of imines. Is it possible?

It is known that sodium metal in ethanol with toluene under reflux can reduce nitriles to amines1 and can also reduce oximes and schiff bases to primary amines and secondary amines respectively2. Is it possible to reduce primary imines where $\ce{R1R2C=N-H}$ or $\ce{R1R2C=NMgBr}$(imine anion) to amines? I have of yet not yet been able to find literature confirming this.


**References**


1. Walter, L. A.; McElvain, S. M. (**1934**). The Reduction of Cyanides. Journal of the American Chemical Society, 56(7), 1614–1616. doi:[10.1021/ja01322a051](https://sci-hub.hkvisa.net/10.1021/ja01322a051)
2. The Reduction of Aliphatic Cyanides and Oximes with Sodium and n-Butyl Alcohol, C. M. Suter and Eugene W. Moffett, Journal of the American Chemical Society **1934** 56 (2), 487-487
DOI: [10.1021/ja01317a502](https://pubs.acs.org/doi/10.1021/ja01317a502)




I couldn't find a paper which directly discusses imine reduction with the help of sodium metal and alcohol but I did found its mention in a different paper which discusses the reduction using calcium and ethanol. I believe sodium metal follows similar reaction pathway.



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> The reduction of imines is one of the most significant and useful methods for preparation of the corresponding amines. Many reduction processes were therefore widely investigated, which include catalytic reduction as well as the use of metal hydrides ($\ce{LiAlH4, NaBH4}$ or others) transition metals complexes (such as iridium, rhodium, molybdenum, nickel, tin, titanium, ruthenium, samarium), different boron compounds or complexes **or metal reduction systems- metal (Na, Zn, Al or Mg) in alcohols, alkaline or acidic aq. solution.** Most of the general methods of imine reduction present several disadvantages in the view of cost, safety and operations. As a solution to these problems, we paid much attention to the reduction of imines in water or alcohol as both hydrogen source and solvent. Now, we wish to report the reduction of aromatic and aliphatic imines using metallic calcium in ethanol.
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> [![enter image description here](https://i.stack.imgur.com/9YUey.png)](https://i.stack.imgur.com/9YUey.png)
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**Ref.:** RAPID AND CONVENIENT APPROACH TO AMINES: REDUCTION
OF IMINES USING METALLIC CALCIUM IN ETHYLALCOHOL, Yoshiharu MITOMA, Naoyoshi EGASHIRA, Cristian SIMION and Masashi TASHIRO, Revue Roumaine de Chimie, **2006**, 51(7-8), 839–842 ([link](https://revroum.lew.ro/wp-content/uploads/2006/RRC_7-8_2006/Art%2032.pdf))


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