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Methyl 2-cyanobenzoate → (2-(Aminomethyl)phenyl)methanol

HRID 582576
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HRID 582576 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[N:11].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[NH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]
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참가 물질

4

반응물 2

HCID 582554Methyl 2-cyanobenzoateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 11275036(2-(Aminomethyl)phenyl)methanol수율 81.8%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

실험 절차

A solution of methyl-2-cyanobenzoate (10 g, 62.11 mmol) in ethyl ether (300 mL) was added dropwise to a slurry of lithium aluminum hydride in ethyl ether (200 mL). After the addition was complete, more ether was added (200 mL) and the mixture heated at reflux for 2 h. The cooled reaction mixture was quenched by careful addition of succesive amounts of water (7.1 mL), 1N sodium hydroxide solution (7.1 mL) and water (21.3 mL). The reaction was filtered and evaporated to give 6.96 g (50.8 mmol) of 2-(aminomethyl)benzyl alcohol. This material was carried on without further purification.

후처리

  1. additionAfter the addition
  2. temperaturethe mixture heated
  3. temperatureat reflux for 2 h
  4. customThe cooled reaction mixture
  5. customwas quenched by careful addition of succesive amounts of water (7.1 mL), 1N sodium hydroxide solution (7.1 mL) and water (21.3 mL)
  6. filtrationThe reaction was filtered
  7. customevaporated

출처 및 근거

ORD 기록
ord-9961a782de6f450db167dc0f29472df2
출처 데이터셋
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05925635

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