I want to try a Doebner-Miller Synthesis reaction without using nitrobenzene or any other oxidizing agent. I want to end up the reaction with non aromatization of nitrogen containing ring. Can anybody suggest me best available catalyst (even acid like H2SO4/HCl) and detail procedure (time, temperature etc.) for this reaction.
Dear Sachin Wazalwar thank you for your very interesting technical question. Just in case that this is still of interest to you I can recommend to you an alternative procedure. It is generally well-established that the Doebner-Miller Synthesis reaction requires the use of an oxidizing agent such as nitrobenzene or elemental iodine. I just came across a potentially useful research article in which an improved synthetic procedure is reported which does not require the use of an oxidizing agent. The article is entitled
An Improvement in the Doebner-Miller Synthesis of Quinaldines
(see attached)
In this variant of the Doebner-Miller Synthesis the reaction is carried out in the presence of zinc chloride (ZnCl2). This leads to formation of ZnCl2 hydrochloride complexes of the resulting heterocyclic compounds. In a second step these complexes are easily decomposed by addition of aqueous ammonia. The straigtforward method is certainly worth a try.
Good luck! 👍
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