Acetic Anhydride → 4-Acetamido-2-fluorobenzoic acid

HRID 1406466Notes

Reaction equation

HRID 1406466 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(O)(=O)C.O>[C:12]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 3026804-Amino-2-fluorobenzoic acid

Product 1

HCID 130413704-Acetamido-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-amino-2-fluoro-benzoic acid (5.61 g, 36.2 mmol) and acetic anhydride (5.13 mL, 54.3 mmol) in 60 mL acetic acid was stirred at 60° C. overnight. The mixture was taken up in 250 mL water and stirred for 30 min. The precipitate was filtered and washed with water. The filtrate was washed with ethyl acetate. The organic phase was neutralized with sat. K2CO3 (aq) and concentrated i.vac. A small volume was left, the precipitate was filtered and combined with the first isolated precipitate.

Workup

  1. stirringstirred for 30 min
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. washThe filtrate was washed with ethyl acetate
  5. concentrationconcentrated i.vac
  6. waitA small volume was left
  7. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-5cf10067f3d34ff3907db114aa523b5f
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

Loading…