2-Bromo-4-methylaniline → 2-Amino-5-methylbenzonitrile

HRID 1350505Notes

Reaction equation

HRID 1350505 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH2:9].[C:10]([Cu])#[N:11]>CN1C(=O)CCC1>[NH2:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[C:10]#[N:11]

Participants

4

Reactant 2

HCID 114222-Bromo-4-methylanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 2427782-Amino-5-methylbenzonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Combine 2-bromo-4-methyl-phenylamine (8.00 g, 43.0 mmol), CuCN (4.62 g, 51.6 mmol), and NMP (30.0 ml). Stir the mixture at reflux for 75 minutes then cool it to ambient temperature. Pour the mixture onto ice chips and stir for 1 hour. Remove the resulting precipitate by vacuum filtration. Dissolve the precipitate in NH4OH and extract it with dichloromethane. Combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using dichloromethane/hexanes (75:25) to give 3.39 g (60%) of an orange solid: mass spectrum (ion spray): m/z=133.1 (M+1).

Workup

  1. temperatureat reflux for 75 minutes
  2. additionPour the mixture onto ice chips
  3. stirringstir for 1 hour
  4. customRemove the resulting precipitate
  5. filtrationby vacuum filtration
  6. dissolutionDissolve the precipitate in NH4OH
  7. extractionextract it with dichloromethane
  8. washCombine, wash (brine)
  9. dry with materialdry (sodium sulfate)
  10. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-d7f678ba3e454c9a985f93ab8c0a6f9d
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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