Acetone → 2-Methyl-2-[(4-methylphenyl)amino]propanenitrile

HRID 244970

Reaction equation

HRID 244970 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.[CH3:12][C:13]([CH3:15])=O.C(OCC)(=O)C>C(O)(=O)C>[CH3:12][C:13]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)([CH3:15])[C:1]#[N:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7813p-ToluidineHCID 8857Ethyl AcetateHCID 8929Sodium Cyanide

Product 1

HCID 212392432-Methyl-2-[(4-methylphenyl)amino]propanenitrileYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium cyanide (0.735 g, 15 mmol) was added to a mixture of p-toluidine (1.07 g, 10 mmol) and acetone (1.16 g, 20 mmol) in 90% acetic acid (10 ml). The reaction mixture was stirred at room temperature for 12 h and then ethyl acetate (50 ml) was added. The organic layer was washed with water (4×30 ml), dried over magnesium sulfate and concentrated under vacuum to dryness to yield 2-methyl-2-(4-methylphenyl)aminopropanenitrile, 5a (1.65 g, 9.5 mmol, 95%) as a brown solid.

Workup

  1. washThe organic layer was washed with water (4×30 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record
ord-c9b08de944a34170aa3db602cbafe2a1
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Linked notes

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