172301-59-6Relevant articles and documents
Synthesis of 3,4-dihydroxy-6-(N-ethylamino)benzamide, a new phenolic compound isolated from green pepper (Piper nigrum L.) berries
Variyar, Prasad S.,Bandyopadhyay, Chiranjib
, p. 911 - 913 (2007/10/03)
The synthesis of 3,4-dihydroxy-6-(N-ethylamino)benzamide (9), a novel phenolic constittuent of green pepper berries, responsible for its blackening during drying process has been developed from vanillic acid (1) in eight steps.Use of mild reaction conditions such as employing anhydrous ammonium formate as hydrogen transfer agent during reduction of 3 at room temperature (Step III), reductive alkylation of 4 with sodium borohydride and acetic acid (Step IV) and protecting the amino group using acetic acid (Step IV) and protecting the amino group using trifluoroacetic acid prior to demethylation (Step VII) and hydrolysis (Step VIII) results in an acceptable yield of the final product (9) despite its highly unstable nature.
