Clearly and neatly, draw a mechanism for the proposed synthesis of the anesthetic procaine (Novocain) in two (2) steps using p-nitrobenzoic acid anhydride (1) and N,N-diethylethanol amine (2). Be sure to note approximate equivalents for each reagent, solvents, all isolable intermediates, and conditions for isolation/ purification of the final product.

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter31: Immunochemistry
Section: Chapter Questions
Problem 31.70P
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Clearly and neatly, draw a mechanism for the proposed synthesis of the anesthetic procaine (Novocain) in two (2) steps using p-nitrobenzoic acid anhydride (1) and N,N-diethylethanol amine (2). Be sure to note approximate equivalents for each reagent, solvents, all isolable intermediates, and conditions for isolation/ purification of the final product. NOTE: A flow chart for purification might be extremely helpful.. 

H₂N-
procaine (Novocain)
-NEt₂
O₂N
1
NO₂
HO
2
NEt₂
Transcribed Image Text:H₂N- procaine (Novocain) -NEt₂ O₂N 1 NO₂ HO 2 NEt₂
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