Anthranilic Acid → 2-Cyclohexylideneamino-benzoic acid

HRID 2251097Notes

Reaction equation

HRID 2251097 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>>[C:11]1(=[N:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 227Anthranilic AcidHCID 7967Cyclohexanone

Product 1

HCID 46156362-Cyclohexylideneamino-benzoic acidYield 69.4%

Procedure

Anthranilic acid (10 g, 73 mmol) and cyclohexanone (9.8 mL, 95 mmol) were dissolved in xylenes (110 mL) in a flask equipped with a Dean-Stark apparatus and heated to reflux over 18 hours. The reaction mixture was cooled to room temperature and the resulting precipitate collected by filtration. The filter cake was washed with hexanes and dried in vacuo to give the desired imine (11 g, 69% yield) as a beige solid.

Workup

  1. customequipped with a Dean-Stark apparatus
  2. temperatureheated
  3. temperatureto reflux over 18 hours
  4. filtrationthe resulting precipitate collected by filtration
  5. washThe filter cake was washed with hexanes
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d553c0b93bf74137ae24610895f8dc5b
Source dataset
uspto-grants-2008_01
Patent number
US07319103B2

Reaction notes

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