Water → 8-Formyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61756Notes

Reaction equation

HRID 61756 reaction equation
O.[CH3:2][C:3]1([CH3:25])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[N:17])[CH:12]=3)[C:7]=2[C:6](=[O:18])[C:5]2[CH:19]=[CH:20][C:21]([CH:23]=C)=[CH:22][C:4]1=2.I([O-])(=O)(=O)=[O:27].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[CH:23]([C:21]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[C:7]3[C:8]4[C:13](=[CH:12][C:11]([C:16]#[N:17])=[CH:10][CH:9]=4)[NH:14][C:15]=3[C:3]([CH3:2])([CH3:25])[C:4]=2[CH:22]=1)=[O:27]

Participants

7

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 668340546,6-Dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Product 1

HCID 866638188-Formyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 77.9%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

To the THF (24 ml) and distilled water (6 ml) suspension of 6,6-dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound B2-24, 600 mg, 1.920 mmol), t-butanol solution of osmium tetraoxide (192 μl, 0.1 eq.) and sodium meta periodate (821 mg, 2.0 eq.) were added and the mixture was stirred at room temperature for 3 hr. Aqueous solution of sodium thiosulfate (0.3 M) was added to the solution, which was then extracted with an ethyl acetate. The organic layer was washed with 10% aqueous solution of disodium ethylenediamine tetraacetic acid. The organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (470 mg, 77%).

Workup

  1. distillationTo the THF (24 ml) and distilled
  2. additionwere added
  3. extractionwas then extracted with an ethyl acetate
  4. washThe organic layer was washed with 10% aqueous solution of disodium ethylenediamine tetraacetic acid
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe residues obtained
  8. concentrationafter concentration under reduced pressure
  9. customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3ca81289ebd1423aac62c033e48c8769
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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