2-Bromo-4-isopropylaniline → 2-Amino-5-isopropylbenzonitrile

HRID 1350498Notes

Reaction equation

HRID 1350498 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[NH2:14]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:14][C:6]1[CH:7]=[CH:8][C:9]([CH:11]([CH3:13])[CH3:12])=[CH:10][C:5]=1[C:2]#[N:3]

Participants

5

Reactant 2

HCID 5213372-Bromo-4-isopropylanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 210934632-Amino-5-isopropylbenzonitrileYield 88.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a mixture of copper (I) cyanide (2.5 g, 28.02 mmol), and 2-bromo4-isopropyl-phenylamine (5.0 g, 23.35 mmol) in 1-methyl-2-pyrrolidinone (20 ml) to 195° C. for four hours. Dilute the reaction mixture with 100 ml of ethyl acetate and wash the dark solution twice with 28% aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride (brine) and twice with water. Collect the organic layer, dry over sodium sulfate and remove the solvent under reduced pressure. Purify the residue via flash chromatography eluting with a step gradient starting with hexanes and going to 80% hexanes with 20% ethyl acetate to obtain 3.31 g (20.66 mmol, 88% yield) of the title compound as an orange oil: Mass Spectrum (m/e): 161(M+1).

Workup

  1. temperatureHeat
  2. washwash the dark solution twice with 28% aqueous ammonium hydroxide
  3. customCollect the organic layer
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure
  6. customPurify the residue via flash chromatography
  7. washeluting with a step gradient

Sources & evidence

ORD record
ord-23a8ff61cfd74c8dadc59914e367b874
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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