Benz[cd]indol-2(1H)-one, 1-methyl- → Benz(cd)indol-2(1H)-one, 2a,3,4,5-tetrahydro-1-methyl-

HRID 276906Notes

Reaction equation

HRID 276906 reaction equation
[CH3:1][N:2]1[C:10]2[C:5]3[C:6](=[CH:11][CH:12]=[CH:13][C:4]=3[C:3]1=[O:14])[CH:7]=[CH:8][CH:9]=2>[Ni].C(O)C>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]3[CH2:11][CH2:12][CH2:13][CH:4]([C:5]=23)[C:3]1=[O:14]

Participants

4

Reactant 1

HCID 121175Benz[cd]indol-2(1H)-one, 1-methyl-

Product 1

HCID 11008652Benz(cd)indol-2(1H)-one, 2a,3,4,5-tetrahydro-1-methyl-Yield 80%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Ethanol and Raney nickel slurry (Aldrich) were added to 1-methyl-benz[cd]indole-2(1H)-one (4.5 g, 25 mmol) to carry out catalytic reduction under ordinary pressure. The reaction was terminated when 1.15 L of hydrogen absorption was observed, Raney nickel was removed by filtration, the resulting filtrate was concentrated and then the thus obtained colorless oil was purified by a silica gel column chromatography to obtain 3.8 g of the title compound (20 mmol, 80% in yield).

Workup

  1. customThe reaction was terminated
  2. customwhen 1.15 L of hydrogen absorption
  3. customRaney nickel was removed by filtration
  4. concentrationthe resulting filtrate was concentrated
  5. customthe thus obtained colorless oil was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-da4cbe0389154ab39f826a46030c9e97
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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