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

HRID 131322

反応式

HRID 131322 の反応式
[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]

参加物

5

反応物 2

HCID 5213372-Bromo-4-isopropylanilineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 210934632-Amino-5-isopropylbenzonitrile収率 88.5%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ddbd8bc91ad648baaf64d5f6433256b3
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

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