Sodium Bicarbonate → HCID 19592298, compound

HRID 613497Notes

Reaction equation

HRID 613497 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[CH:17]=C)=[O:5].I([O-])(=O)(=O)=[O:25].[Na+].C(=O)(O)[O-].[Na+]>O1CCOCC1.O.C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[CH:17]=[O:25])=[O:5]

Participants

8

Reactant 3

HCID 516892Sodium BicarbonateHCID 19592712HCID 19592712, compoundHCID 23667635Sodium periodate

Product 1

HCID 19592298HCID 19592298, compoundYield 56.3%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 8-(2,6-dichlorobenzoylamino)-4-vinylquinoline (150 mg) in dioxane and water was added catalytic amount of osmium tetroxide in tert-butanol under ice-cooling, and the mixture was stirred for 5 minutes. To the mixture was added sodium periodate (206 mg) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature and for 6 hours at ambient temperature. To the mixture was added saturated sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (dichloromethane-n-hexane) to give 8-(2,6-dichlorobenzoylamino)-4-formylquinoline (85 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 30 minutes at the same temperature and for 6 hours at ambient temperature
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography (dichloromethane-n-hexane)

Sources & evidence

ORD record
ord-b73f8ed5f4ed42b0886cdf907a9b8f68
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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