Acetic Anhydride → 2-Acetamido-3-methylbenzoic acid

HRID 2427100Notes

Reaction equation

HRID 2427100 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](OC(=O)C)(=[O:14])[CH3:13].O1CCCC1>O>[C:12]([NH:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 781012-Amino-3-methylbenzoic acid

Product 1

HCID 126392042-Acetamido-3-methylbenzoic acidYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.51 g of 2-amino-3-methylbenzoic acid, 1.0 g of acetic anhydride and 20 ml of tetrahydrofuran was stirred at 80° C. for 13 hours. The reaction mixture was allowed to cool to room temperature, poured into water, and extracted with ethyl acetate two times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was washed with ethyl acetate to obtain 0.72 g of 2-acetylamino-3-methylbenzoic acid of the formula:

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate two times
  3. washwashed successively with water
  4. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-dc0d8bc0053f4d54b7eb9f859b96b776
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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