Acetic Acid → 1-p-Tolylaminocyclohexanecarbonitrile

HRID 244993Notes

Reaction equation

HRID 244993 reaction equation
[C-:1]#[N:2].[Na+].C(O)(=O)[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH2:7].[CH3:14][C:15]([CH3:17])=O.C(O[CH2:22][CH3:23])(=O)C.[C:24](O)(=O)[CH3:25]>>[CH3:14][C:15]1[CH:17]=[CH:23][C:22]([NH:7][C:6]2([C:1]#[N:2])[CH2:5][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:25][CH:24]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 227Anthranilic AcidHCID 8857Ethyl AcetateHCID 8929Sodium Cyanide

Product 1

HCID 598390991-p-TolylaminocyclohexanecarbonitrileYield 90%

Procedure

Sodium cyanide (0.245 g, 5 mmol) was added to a mixture of anthranilic acid (0.411 g, 3 mmol) and acetone (1 ml, 13.6 mmol) in acetic acid 90% (3 ml). The reaction mixture was stirred at room temperature for 12 h and then 50 ml of ethyl acetate was added. The organic layer was washed with brine (3×30 ml). The organic layer was dried over magnesium sulfate, concentrated and chromatographed (dichloromethane:acetone, 90:10) to yield 22a (0.551 g, 2.7 mmol, 90%) as a brown solid.

Workup

  1. washThe organic layer was washed with brine (3×30 ml)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customchromatographed (dichloromethane:acetone, 90:10)

Sources & evidence

ORD record
ord-0566c8866383460bb58fa21b4895da00
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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