Acetic Anhydride → 2-acetamido-5-fluorobenzoic acid

HRID 439321Notes

Reaction equation

HRID 439321 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[C:12]([NH:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 27358272-acetamido-5-fluorobenzoic acid

Procedure

To a flask containing acetic anhydride (60 mL) was slowly added 2-amino-5-fluorobenzoic acid (7.68 g, 0.05 mol) over 20 minutes and continued to stir over 2 hours at room temperature. The product was collected by filtration and allowed to dry to give 2-acetamido-5-fluorobenzoic acid (8.03 g, 82) as an off white solid.: m.p. 168°-170°; 1H NMR (400 MHz, DMSO-d6) δ 2.11 (s, 3H), 7.46 (dt, 1H), 7.65 (dd, 1H), 8.41 (dd, 1H), 10.83 (s, 1H); 13C NMR (100 MHz, DMSO-d6) δ 25.3, 117.1, 117.4, 119.3, 121.2, 121.4, 122.9, 137.6, 156.0, 158.4, 168.7, 168.9.

Workup

  1. customover 20 minutes
  2. filtrationThe product was collected by filtration
  3. customto dry

Sources & evidence

ORD record
ord-a1f9e26abf414e5ab4007ff731317a99
Source dataset
uspto-grants-1996_05
Patent number
US05514676

Reaction notes

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