Acetic Anhydride → 3-Acetamidophthalic Anhydride

HRID 1050728Notes

Reaction equation

HRID 1050728 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[C:11]([OH:13])=[O:12].[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]2[C:5]([O:13][C:11](=[O:12])[C:3]=12)=[O:7])(=[O:16])[CH3:15]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 794903-Aminophthalic acid

Product 1

HCID 2261213-Acetamidophthalic AnhydrideYield 61%

Procedure

A mixture of 3-aminophthalic acid (108 g, 596 mmol) and acetic anhydride (550 mL) was charged into a 1-L 3-necked round bottom flask equipped with a mechanical stirrer, a thermometer, and a condenser. The reaction mixture was refluxed for 3 hours, cooled to ambient temperature, and kept at 0-5° C. for another 1 hour. The crystalline solid was collected by vacuum filtration and washed with ether. The solid product was dried in vacuum at ambient temperature to a constant weight to yield 75 g (61% yield) of 3-acetamidopthalic anhydride as a white product. The product in CDCl3 was characterized by a 1H NMR spectrum showing the following chemical shifts (δ in ppm): 2.21 (s, 3H), 7.76 (d, 1H), 7.94 (t, 1H), 8.42 (d, 1H), 9.84 (s, 1H).

Workup

  1. additionwas charged into a 1-L 3-necked round bottom flask
  2. customequipped with a mechanical stirrer
  3. temperatureThe reaction mixture was refluxed for 3 hours
  4. filtrationThe crystalline solid was collected by vacuum filtration
  5. washwashed with ether
  6. customThe solid product was dried in vacuum at ambient temperature to a constant weight

Sources & evidence

ORD record
ord-90c0d472d06b4e839a3f5eecf5a008c4
Source dataset
uspto-grants-2016_07
Patent number
US09387195B2

Reaction notes

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