Dimethyl 5-nitroisophthalate → Dimethyl 5-aminoisophthalate

HRID 730253

Reaction equation

HRID 730253 reaction equation
Cl.SC1C(N)=CC(C(O)=O)=CC=1C(O)=O.[N+:16]([C:19]1[CH:20]=[C:21]([C:29]([O:31][CH3:32])=[O:30])[CH:22]=[C:23]([CH:28]=1)[C:24]([O:26][CH3:27])=[O:25])([O-])=O>>[CH3:27][O:26][C:24](=[O:25])[C:23]1[CH:28]=[C:19]([NH2:16])[CH:20]=[C:21]([C:29]([O:31][CH3:32])=[O:30])[CH:22]=1

Participants

3

Reactant 2

HCID 83316Dimethyl 5-nitroisophthalateHCID 689933964-Mercapto-5-aminoisophthalic acid hydrochloride

Product 1

HCID 66831Dimethyl 5-aminoisophthalate

Procedure

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.

Sources & evidence

ORD record
ord-99526760e68845849d3b49efed3e0f55
Source dataset
uspto-grants-2009_09
Patent number
US07582719B1

Linked notes

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