Dimethyl 5-nitroisophthalate → Dimethyl 5-aminoisophthalate

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Reaction Steps

The AB2 monomer, 4-mercapto-5-aminoisophthalic acid hydrochloride, is synthesized in similar fashion, starting with catalytic hydrogenation of dimethyl 5-nitroisophthalate to form the corresponding amine, dimethyl-5-aminoisophthalate, which is then acetylated to protect the amino group. Dimethyl-5-aminoisophthalate is treated with thiocyanogen bromide (generated in-situ from bromine and ammonium thiocynate), and finally hydrolyzed to provide the desired monomer.

Provenance & Evidence