Water → 2-Acetamido-6-methylbenzoic acid

HRID 22180

Reaction equation

HRID 22180 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH2:11])[CH:5]=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].O>C(O)(=O)C>[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1512106-Methylanthranilic acid

Product 1

HCID 28014002-Acetamido-6-methylbenzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 15.2 g (100 mmoles) of 6-methyl-2-aminobenzoic acid (obtained from the Aldrich Chemical Company, Inc., Milwaukee Wis.) in 150 mL of glacial acetic acid was heated in a water bath to promote homogeneity. Acetic anhydride, 15 mL (159 mmole), was added and the resultant solution kept in the hot water bath for 40 minutes. Upon cooling to near room temperature, the dark solution was poured over crushed ice. When all ice had melted, the pale beige solid which had separated was collected and air-dried. 16.4 g (85% yield) 6-methyl-2-acetylaminobenzoic acid was obtained. NMR(DMSO-d6): 2.00(s,3H), 2.33(s,3H), 7.05(d,1H,J=7.5 Hz), 7.29(t,1H,J=7.8 Hz), 7.41(d,1H,J=7.8 Hz), 9.60(bs,1H). MS(m/z): 193(M+).

Workup

  1. customobtained from the Aldrich Chemical Company, Inc
  2. additionthe dark solution was poured
  3. customover crushed ice
  4. customthe pale beige solid which had separated
  5. customwas collected
  6. customair-dried

Sources & evidence

ORD record
ord-85be81655f494bafa55a59b2988ed5cb
Source dataset
uspto-grants-1995_06
Patent number
US05428021

Linked notes

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