Acetic Acid → Anthranil

HRID 1870728Notes

Reaction equation

HRID 1870728 reaction equation
[N+:1]([C:4](=O)[C:5]1C=C[CH:8]=[CH:7][CH:6]=1)([O-])=O.C1(O)C=CC=CC=1.[C:19]([OH:22])(=O)[CH3:20]>>[N:1]1[O:22][CH:19]=[C:20]2[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]2

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 996PhenolHCID 14491740HCID 14491740, compound

Product 1

HCID 67498AnthranilYield 66%

Conditions

Temperature
0 °C

Procedure

α-Nitrobenzaldehyde (15.1 g, 0.100 mol) and phenol 9.46 (0.100 mol) were dissolved in 120 mL of glacial acetic acid in a three-necked round bottom flask. The flask was flushed with N2 (g), and the solution was cooled to 0° C. HCl (g) was bubbled through the solution and then through a sodium hydroxide solution to neutralize the acid. The reaction flask was fitted with a rubber stopper and the solution was allowed to warm to ambient temperature and then stirred for 2 h. HCl (g) was removed by bubbling N2 (g) through the solution. The resulting precipitate was filtered and washed with 15 mL of glacial acetic acid to afford 16.2 g (66%) of anthranil. The anthranil was directly reduced to 2-Amino-5-chloro-4'-hydroxybenzophenone (below) without further purification.

Workup

  1. customThe flask was flushed with N2 (g)
  2. customHCl (g) was bubbled through the solution
  3. customThe reaction flask was fitted with a rubber stopper
  4. temperatureto warm to ambient temperature
  5. customHCl (g) was removed
  6. customby bubbling N2 (g) through the solution
  7. filtrationThe resulting precipitate was filtered
  8. washwashed with 15 mL of glacial acetic acid

Sources & evidence

ORD record
ord-7b6f871bdd8143e892ff6abc0929ed42
Source dataset
uspto-grants-2000_08
Patent number
US06100254

Reaction notes

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