Paragraph for Question Nos. 12 and 14
Dolacaine, a local anesthetic, is a compound with molecular formula, C13 H20 O2 N2 . It is insoluble in water and dilute NaOH, but soluble in dil. HCl. Upon treatment with NaNO2 and HCl and then withβ -naphthol, a highly coloured solid is formed. When Novocaine is boiled with aqueous NaOH , it slowly dissolves. The alkaline solution is shaken with ether and layers are separated.
Acidification of the aqueous layer causes the precipitation of white solid ‘A’; continued addition of acid causes ‘A’ to redissolve. Upon isolation ‘A’ is found to have melting point of 185 -186° C and the formula C7 H7 O2 N : Evaporation of ether layer leaves a liquid ‘B’ of formula C6 H15 ON. with acetic anhydride gives 'C' C8 H17 O2 N which is insoluble in water and dilute bases, but soluble in dilute HCl. ‘B’ is found to be identical to the compound formed by the action of diethylamine on ethylene oxide.
When compound ‘B’ is treated with p – nitrobenzoyl chloride followed by moderate reduction with Ni/H2 ; the compound formed is