p-Toluidine → 1-p-Tolylaminocyclohexanecarbonitrile

HRID 244982Notes

Reaction equation

HRID 244982 reaction equation
[C-:1]#[N:2].[Na+].[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(OCC)(=O)C>C(O)(=O)C>[CH3:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:12]2([C:1]#[N:2])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 7967CyclohexanoneHCID 8857Ethyl AcetateHCID 8929Sodium Cyanide

Product 1

HCID 598390991-p-TolylaminocyclohexanecarbonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanide (0.147 g, 3 mmol) was added to a mixture of p-toluidine (0.214 g, 2 mmol) and cyclohexanone (0.294 g, 3 mmol) in acetic acid 90% (3 ml). The reaction mixture was stirred at room temperature for 12 h and then 20 ml of ethyl acetate was added. The organic layer was washed with water (3×10 ml), dried over magnesium sulfate and concentrated under vacuum to dryness to yield 1-(4-methylphenyl)aminocyclohexanenitrile, 9a (0.398 g, 1.86 mmol, 93%) as a brown solid.

Workup

  1. washThe organic layer was washed with water (3×10 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record
ord-540482f75dd243c79996ce8367492cc5
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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