Novocaine, a local anesthetic, is a compound of formula \(\mathrm{C}_{13}
\mathrm{H}_{20} \mathrm{O}_{2} \mathrm{~N}_{2}\). It is insoluble in water and
dilute \(\mathrm{NaOH}\), but soluble in dilute HC1. Upon treatment with
\(\mathrm{NaNO}_{2}\) and \(\mathrm{HCl}\) and then with \(\beta\) -naphthol, a
highly colored solid is formed. When Novocaine is boiled with aqueous
\(\mathrm{NaOH}\), it slowly dissolves. The alkaline solution is shaken with
ether and the layers are separated. Acidification of the aqueous layer causes
the precipitation of a white solid A; continued addition of acid causes \(A\) to
redissolve. Upon isolation \(A\) is found to have a melting point of
\(185-6^{\circ}\) and the formula \(\mathrm{C}_{7} \mathrm{H}_{7} \mathrm{O}_{2}
\mathrm{~N}\). Evaporation of the ether layer leaves a liquid \(\mathrm{B}\) of
formula \(\mathrm{C}_{6} \mathrm{H}_{15} \mathrm{ON}\). B dissolves in water to
give a solution that turns litmus blue. Treatment of \(B\) with acetic anhydride
gives C, \(\mathrm{C}_{8} \mathrm{H}_{17} \mathrm{O}_{2} \mathrm{~N}\), which is
insoluble in water and dilute base, but soluble in dilute HCl. \(\mathrm{B}\) is
found to be identical with the compound formed
by the action of diethylamine on ethylene oxide.
(a) What is the structure of Novocaine?
(b) Outline all steps in a complete synthesis of Novocaine from toluene and
readily available aliphatic and inorganic reagents.
$$
\begin{array}{|l|l|l|}
\hline {\text { CARBOXYLIC ACIDS }} \\
\hline \text { Name } & \text { Formula } & \begin{array}{c}
\text { M.p. } \\
{ }^{\circ} \mathrm{C}
\end{array} \\
\hline \text { o-Nitrobenzoic } & \circ-\mathrm{O}_{2} \mathrm{NC}_{6}
\mathrm{H}_{4} \mathrm{COOH} & 147 \\
\hline \text { m-Nitrobenzoic } & \mathrm{m}-\mathrm{O}_{2} \mathrm{NC}_{6}
\mathrm{H}_{4} \mathrm{COOH} & 141 \\
\hline \text { p-Nitrobenzoic } & \mathrm{p}-\mathrm{O}_{2} \mathrm{NC}_{6}
\mathrm{H}_{4} \mathrm{COOH} & 242 \\
\hline \text { Phthalic } & \mathrm{o}-\mathrm{C}_{6}
\mathrm{H}_{4}(\mathrm{COOH})_{2} & 231 \\
\hline \text { Isophthalic } & \mathrm{m}-\mathrm{C}_{6}
\mathrm{H}_{4}(\mathrm{COOH})_{2} & 348 \\
\hline \text { Terephthalic } & \mathrm{p}-\mathrm{C}_{6}
\mathrm{H}_{4}(\mathrm{COOH})_{2} & 300 \text { sub1. } \\
\hline \text { Salicylic } & \mathrm{o}-\mathrm{HOC}_{6} \mathrm{H}_{4}
\mathrm{COOH} & 159 \\
\hline \text { p-Hydroxybenzoic } & \mathrm{p}-\mathrm{HOC}_{6} \mathrm{H}_{4}
\mathrm{COOH} & 213 \\
\hline \text { Anthranilic } & \mathrm{o}-\mathrm{H}_{2} \mathrm{NC}_{6}
\mathrm{H}_{4} \mathrm{COOH} & 146 \\
\hline \text { m-Aminobenzoic } & \mathrm{m}-\mathrm{H}_{2} \mathrm{NC}_{6}
\mathrm{H}_{4} \mathrm{COOH} & 179 \\
\hline \text { p-Aminobenzoic } & \mathrm{p}-\mathrm{H}_{2} \mathrm{NC}_{6}
\mathrm{H}_{4} \mathrm{COOH} & 187 \\
\hline \text { o-Methoxybenzoic } & \mathrm{o}-\mathrm{CH}_{3} \mathrm{OC}_{6}
\mathrm{H}_{4} \mathrm{COOH} & 101 \\
\hline \text { m-Methoxybenzoic } & \mathrm{m}-\mathrm{CH}_{3} \mathrm{OC}_{6}
\mathrm{H}_{4} \mathrm{COOH} & 110 \\
\hline \text { p-Methoxybenzoic(Anisic) } & \mathrm{p}-\mathrm{CH}_{3}
\mathrm{OC}_{6} \mathrm{H}_{4} \mathrm{COOH} & 184 \\
\hline
\end{array}
$$
