Acetic Anhydride → 3-Acetamino-4-methoxycarbonylbenzoic acid

HRID 2103809Notes

Reaction equation

HRID 2103809 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[C:12]([OH:14])=[O:13]>C(O)(=O)C>[NH:8]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[C:12]([OH:14])=[O:13])[C:1]([CH3:2])=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 52355003-Amino-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 670502013-Acetamino-4-methoxycarbonylbenzoic acidYield 89.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic anhydride (1.89 mL, 20 mmol) was added to a suspension of 3-amino-4-methoxycarbonylbenzoic acid (1.95 g, 10 mmol) in acetic acid (10 mL), and the mixture was heated with reflux for 6 hours. After cooling, the precipitated solid was filtered to obtain 2.12 g of the desired product as a colorless solid (yield 89%).

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 6 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-2e104f921b784468889c0e54e501c6c9
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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