Question

Name Lidocaine (right) is a commonly used local anesthetic and is listed as one of the WHO's essential medicines. It can be prepared from 2,6-dimethylaniline Lab Section 3. ( YNNへ (2pt) Propose a synthesis for 2,6-dimethylaniline starting with m-xylene. Show each isolated intermediate and give the reagents required over the reaction arrows. a. b. (1 pt) Explain why the yield of this reaction would be poor using the reactions you know-A vanadium catalyzed version of this reaction gives much better yields.

Answer 1

m-xylene undergo nitration with nitric acid in the presence of sulfuric acid produce 1, 3-dimethyl-2-nitrobenzene. Which undergo reduction with Sn/HCl produces desired product that is 2,6-dimethylaniline. Aromatic compounds undergo electrophilic substitution reaction, the electrophile in nitration of aromatic compounds is nitronium ion is as follows Generation of nitronium ion is as follows: HNO3 + H2S04 Rightarrow H_2O + NO_2^+ + HSO_4 Due to formation of mixture of isomers the percentage of yield reduces