Phenylacetonitrile → 2-Amino-3-phenylpropanenitrile

HRID 1029813

반응식

HRID 1029813 반응식
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[C-:20]#[N:21].C([Al+]CC)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO>[NH2:9][CH:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:20]#[N:21]

참가 물질

7

반응물 4

HCID 8794PhenylacetonitrileHCID 24436Sodium SulfateHCID 16686413Diethyl aluminum cyanideHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 5613842-Amino-3-phenylpropanenitrile수율 65%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

10 millimoles (1.17 g) of benzyl cyanide are dissolved in 0 ml of anhydrous toluene at 0° C., under an argon atmosphere. 15 millimoles of 1.5M toluenic solution of diisobutylaluminum hydride (10 ml) are added, dropwise, at this temperature. The temperature is maintained at 0° C. for one hour, then 13.7 ml (viz 1.5 eq) of diethyl-aluminum cyanide are added. The reaction mixture is stirred for 3 hours while the temperature reaches the room temperature. Then it is hydrolyzed with 10 ml of methanol, and with a slurry of sodium sulfate. After purification of the so-obtained α-aminonitrile, by high pressure liquid chromatrography on silica, with elution by ethyl acetate/petroleum ether, there are obtained 0.95 g of 2-amino -3-phenyl-propionitrile, in the form of an orange-colored oil, yield: 65%.

후처리

  1. customthe room temperature
  2. customAfter purification of the so-obtained α-aminonitrile
  3. washby high pressure liquid chromatrography on silica, with elution by ethyl acetate/petroleum ether, there

출처 및 근거

ORD 기록
ord-c93198bb29f5494c90026b63267afeb3
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05103019

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