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

HRID 131312

반응식

HRID 131312 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 2427782-Amino-5-methylbenzonitrile수율 60%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Combine 2-bromo-4-methyl-phenylamine (8.00 g, 43.0 mmol), CuCN (4.62 g, 51.6 mmol), and NMP (30.0 ml) and stir at reflux. After 75 minutes, cool 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 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).

후처리

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

출처 및 근거

ORD 기록
ord-04bb8768009749168397a3561c82c357
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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