Stannous Chloride → 4-Amino-3-methylbenzonitrile

HRID 2753

반응식

HRID 2753 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[C:5]#[N:6].Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCO.CCOC(C)=O>[NH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[CH3:1]

참가 물질

6

반응물 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 28014343-Methyl-4-nitrobenzonitrile

생성물 1

HCID 70103164-Amino-3-methylbenzonitrile수율 70.7%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.3 mmol) in 100 mL of EtOH is added SnCl2 (13.9 g, 61.7 mmol). The resulting solution is heated at reflux. After 2 h, the solution is cooled to ambient temperatures. The solution is poured into 150 mL of ice water. The pH of the solution is adjusted to >7 with a solution of saturated NaHCO3. The solution is diluted with EtOAc and the resulting mixture is filtered through Celite. The filtered solution is separated. The organic layer is dried over MgSO4, filtered and concentrated to give the title compound (1.57 g, 8.7 mmol) as an off-white solid.

후처리

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux
  3. temperaturethe solution is cooled to ambient temperatures
  4. filtrationthe resulting mixture is filtered through Celite
  5. customThe filtered solution is separated
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-68a8e77da56c464fb8e4488b01b277d1
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731315

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