2-Nitrocinnamaldehyde
Introduction '''2-Nitrocinnamaldehyde''', '''''ortho''-nitrocinnamaldehyde''' or '''''o''-nitrocinnamaldehyde''' is an organic aromatic compound containing a nitro group ortho- to the 1-position of cinnamaldehyde.
Synthesis 2-Nitrocinnamaldehyde can be synthesized by dissolving cinnamaldehyde to a solution of acetic anhydride in acetic acid, and adding a stoichiometric amount of concentrated nitric acid at 0–5 °C. Yields are around 36-46% of theoretical.Nitration of cinnamaldehyde via acidification of a nitrate salt with H2SO4 also yields the ortho-nitro compound, however it also yields some of the para-nitro compound, which is generally undesired.2-Nitrocinnamaldehyde can also be prepared by reacting 2-nitrobenzaldehyde with acetaldehyde in a condensation reaction.
Uses 2-Nitrocinnamaldehyde can be oxidized to 2-nitrocinnamic acid which can be used in the Baeyer-Emmerling indole synthesis to produce indole and substituted indoles.
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