Water → 2-Acetamido-6-methylbenzoic acid

HRID 22180

Reaktionsgleichung

Reaktionsgleichung von HRID 22180
[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

Komponenten

5

Edukt 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1512106-Methylanthranilic acid

Produkt 1

HCID 28014002-Acetamido-6-methylbenzoic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-85be81655f494bafa55a59b2988ed5cb
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428021

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