Aniline → 2-Anilino-2-methylpropiononitrile

HRID 2233673Notes

Reaction equation

HRID 2233673 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]([CH3:13])(O)[C:10]#[N:11]>C(OCC)(=O)C>[CH3:8][C:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:13])[C:10]#[N:11]

Participants

4

Reactant 2

HCID 6115AnilineHCID 6406Acetone Cyanohydrin

Product 1

HCID 751282-Anilino-2-methylpropiononitrileYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of aminobenzene (0.931 g, 10 mmol) and acetone cyanohydrin (2 ml) was heated to reflux and stirred for 20 h. After being cold to room temperature, the reaction mixture was poured into ethyl acetate (40 ml) and washed with cold water (2×30 ml). The organic layer was dried over MgSO4, concentrated under vacuum to dryness to yield 2-methyl-2-phenylaminopropanenitrile, 6a (1.51 g, 9.4 mmol, 94%) as slurry brown liquid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customAfter being cold to room temperature
  4. washwashed with cold water (2×30 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record
ord-a7a5c2743434414198213b62a7f86232
Source dataset
uspto-grants-2010_05
Patent number
US07709517B2

Reaction notes

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