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

HRID 33197

Reaction equation

HRID 33197 reaction equation
[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

Participants

4

Reactant 1

HCID 69180o-Phenylenediacetonitrile

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b496c791c22a479b833bb2b691e70546
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Linked notes

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