Acetyl chloride → 4-Acetamido-3-chlorobenzoic acid

HRID 900574Notes

Reaction equation

HRID 900574 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11].[C:12](Cl)(=[O:14])[CH3:13]>C1COCC1>[C:12]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 172114-Amino-3-chlorobenzoic acid

Product 1

HCID 6809514-Acetamido-3-chlorobenzoic acidYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-3-chloro-benzoic acid (10.0 g, 58.3 mmol) in anhydrous THF (100 mL) was added acetyl chloride (20.7 ml, 291.1 mmol) and the solution stirred at room temperature for 48 hours. The solvent was evaporated and the product precipitated from hexanes then filtered and dried to give a white solid (11.73 g, 94% yield). 1H-NMR (500 MHz, CD3OD) δ 2.28 (s, 3H), 7.92 (dd, 1H), 7.99-8.16 (m, 2H). Analytical HPLC (cyano column) 7.84 min.

Workup

  1. customThe solvent was evaporated
  2. customthe product precipitated from hexanes
  3. filtrationthen filtered
  4. customdried

Sources & evidence

ORD record
ord-c6de8aa812ed4ad2b47ed64d6e5e0587
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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