1,2-Benzenedicarboxylic acid, 4-nitro- → N-Hydroxy-4-nitrophthalimide

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=O)[C:7](=[CH:11][CH:12]=1)[C:8](O)=[O:9])([O-:3])=[O:2].P([O-])([O-])([O-])=O.[OH:21][NH3+:22].O[NH3+].O[NH3+]>>[N+:1]([C:4]1[CH:5]=[C:6]2[C:13](=[O:15])[N:22]([OH:21])[C:8](=[O:9])[C:7]2=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 691211,2-Benzenedicarboxylic acid, 4-nitro-

HCID 10176537Hydroxylammonium phosphate (3:1)

Product 1

HCID 11458432N-Hydroxy-4-nitrophthalimide

Procedure

Analogous to Example 4, but from 500 mg (2.37 mmol) of 4-nitrophthalic acid (tech., contaminated with approximately 10% of 3-nitrophthalic acid) and 187 mg (0.974 mmol) of hydroxylammonium phosphate at a bath temperature of 130° C. The yield was 332 mg (67%, approximately 5% contaminated).

Workup

customtemperature of 130° C

Sources & evidence

ORD record: ord-5f980e1714e949f3a1ec2a42ce0bead9
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06316639B1

Reaction notes

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