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

HRID 131322

반응식

HRID 131322 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 210934632-Amino-5-isopropylbenzonitrile수율 88.5%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Heat a mixture of copper (I) cyanide (2.5 g, 28.02 mmol), and 2-bromo-4-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 the dark solution, wash 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 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).

후처리

  1. temperatureHeat
  2. washthe dark solution, wash twice with 28% aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride (brine) and twice with water
  3. customCollect the organic layer
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure
  6. customPurify the via flash chromatography
  7. washeluting with a step gradient

출처 및 근거

ORD 기록
ord-ddbd8bc91ad648baaf64d5f6433256b3
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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