Acetic Anhydride → 3-Acetamidophthalic Anhydride

HRID 32780

Reaction equation

HRID 32780 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%

Conditions

Temperature
2.5 °C

Procedure

A 1 L 3-necked round bottom flask was equipped with a mechanical stirrer, thermometer, and condenser and charged with 3-aminophthalic acid (108 g, 596 mmol) and acetic anhydride (550 mL). The reaction mixture was heated to reflux for 3 hours and cooled to ambient temperature and further to 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 vacua at ambient temperature to a constant weight, giving 75 g (61% yield) of 3-acetamidopthalic anhydride as a white product. 1H-NMR (CDCl3) δ: 2.21 (s, 3H), 7.76 (d, 1H), 7.94 (t, 1H), 8.42 (d, 1H), 9.84 (s, 1H).

Workup

  1. customA 1 L 3-necked round bottom flask was equipped with a mechanical stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 3 hours
  4. filtrationThe crystalline solid was collected by vacuum filtration
  5. washwashed with ether
  6. customThe solid product was dried in vacua at ambient temperature to a constant weight

Sources & evidence

ORD record
ord-2e3edcb0c82b451dbae29a3aae31849e
Source dataset
uspto-grants-2008_09
Patent number
US07427638B2

Linked notes

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