Anthranilic Acid → 2-Cyclohexylideneamino-benzoic acid

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

Reactant 2

HCID 227Anthranilic Acid

HCID 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

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

Sources & evidence

ORD record: ord-d553c0b93bf74137ae24610895f8dc5b
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319103B2

Reaction notes

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