Acetic Anhydride → 5-Acetamidobenzene-1,3-dicarboxylic acid

HRID 2379498Notes

Reaction equation

HRID 2379498 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:14](OC(=O)C)(=[O:16])[CH3:15].CC([O-])=O.[K+]>>[C:14]([NH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8])(=[O:16])[CH3:15]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 668335-Aminoisophthalic acidHCID 517044Potassium Acetate

Product 1

HCID 2422785-Acetamidobenzene-1,3-dicarboxylic acid

Conditions

Temperature
20 °C

Procedure

5-Aminoisophthalic acid (30.33 g, 0.167 mol) was charged into a 250 mL round bottom flask with acetic anhydride (56.24 g, 0.551 mol) and KOAc (0.88 g). The reaction temperature was 60°-110° C. for 45 minutes. The resulting white solid was filtered after the reaction was allowed to cool to room temperature (about 20° C.). Yield 31.98 g (86%). 1H NMR (d-6 DMSO)--10.30, 8.41, 8.14, 2.06. 13C NMR (d-6 DMSO)--69.17, 166.82, 140.16, 131.92, 124,61, 123.59, 24.05.

Workup

  1. filtrationThe resulting white solid was filtered after the reaction

Sources & evidence

ORD record
ord-decfbde445d749adbb189d578d0c7c4d
Source dataset
uspto-grants-1994_11
Patent number
US05362843

Reaction notes

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