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

HRID 2301104Notes

Reaction equation

HRID 2301104 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-

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

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

Workup

  1. customwhen 1.15 L of hydrogen absorption
  2. customRaney nickel was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customthe resulting material was separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-8521ced005804aaaac3f0bd69f66975b
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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