o-Phenylenediacetonitrile → 2,3,4,5-Tetrahydro-1H-benzo(d)azepine

HRID 395263

反応式

HRID 395263 の反応式
[C:1]1([CH2:10][C:11]#[N:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]#N>C(O)C.[Ni]>[CH2:10]1[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[CH2:7][CH2:8][NH:12][CH2:11]1

参加物

4

反応物 1

HCID 69180o-Phenylenediacetonitrile

生成物 1

HCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepine収率 35%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

1,2-Phenylenediacetonitrile (7.5 g, 48 mmol) dissolved in ethanol (150 ml) was added to Raney Ni (2 g) which had been previously washed with ethanol (3×20 ml). The mixture was then hydrogenated at 50° C. at 50 psi pressure with shaking for 24 h. The reaction mixture was then cooled to room temperature and filtered through a pad of kieselguhr and washed through with ethanol (100 ml). The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g), eluting with 2-10% methanol in CH2Cl2 to give the title compound as a brown oil (2.45 g, 35%).

後処理

  1. washhad been previously washed with ethanol (3×20 ml)
  2. customwas then hydrogenated at 50° C. at 50 psi pressure
  3. filtrationfiltered through a pad of kieselguhr
  4. washwashed through with ethanol (100 ml)
  5. customThe filtrate was evaporated in vacuo
  6. customto give a brown oil which
  7. customwas chromatographed on silica gel (100 g)
  8. washeluting with 2-10% methanol in CH2Cl2

出典と根拠

ORDレコード
ord-b7d6ac030fc4475b99e314f89e6f35a4
出典データセット
uspto-grants-2003_08
特許番号
US06605607B1

関連ノート

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