Aniline → 2-Anilino-2-methylpropiononitrile

HRID 1927322Notes

Reaction equation

HRID 1927322 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 (1.51g, 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-54dab045a49a46b88d9399d086b8215f
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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