Ammonia → 4-Amino-3-methylbenzonitrile

HRID 2365435Notes

Reaction equation

HRID 2365435 reaction equation
C[N:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.BrC1C=C[C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1.[Cu](C#N)C#N.N>O>[NH2:13][C:12]1[CH:3]=[CH:4][C:5]([C:6]#[N:2])=[CH:10][C:11]=1[CH3:16]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 114234-Bromo-2-methylanilineHCID 13387N-methyl-2-pyrrolidoneHCID 178418260HCID 178418260, compound

Product 1

HCID 70103164-Amino-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

To an N-methyl-2-pyrrolidone (0.5 L) solution of 4-bromo-2-methylaniline (40 g) was added copper cyanide (38.5 g; 043 moli). The stirred mixture was heated at 200° C. for 2.5 hrs. The mixture was cooled at room temperature then water (1.9 L) and ammonia (0.5 L, 32%) were added. The mixture was extracted with ethyl acetate (2×1.2 L) and the combined organic phases then washed with a mixture of water/ammonia (0.5 L+0.2 L, 32%) and dried over Na2SO4. The solvent was evaporated under vacuum to give the title compound as a brown solid (27.5 g). This material was used in the next step without further purification.

Workup

  1. temperatureThe mixture was cooled at room temperature
  2. extractionThe mixture was extracted with ethyl acetate (2×1.2 L)
  3. washthe combined organic phases then washed with a mixture of water/ammonia (0.5 L+0.2 L, 32%)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-836fee0e4f1c4c2eb24f251f6bdc39bf
Source dataset
uspto-grants-2014_04
Patent number
US08697703B2

Reaction notes

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