Propan-2-one--water (1/1) → 1-(4-Fluorophenyl)-6-formyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 1048875Notes

Reaction equation

HRID 1048875 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]=C)=[CH:15][CH:16]=3)[C:11](=[O:20])[C:10]([C:21]([NH2:23])=[O:22])=[CH:9]2)=[CH:4][CH:3]=1.CC(C)=[O:26].O.I([O-])(=O)(=O)=O.[Na+]>CCOC(C)=O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH:18]=[O:26])=[CH:15][CH:16]=3)[C:11](=[O:20])[C:10]([C:21]([NH2:23])=[O:22])=[CH:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 18366337Propan-2-one--water (1/1)HCID 23667635Sodium periodateHCID 1214478661-(4-Fluorophenyl)-4-oxo-6-vinyl-1,4-dihydroquinoline-3-carboxamide

Product 1

HCID 1214479581-(4-Fluorophenyl)-6-formyl-4-oxo-1,4-dihydroquinoline-3-carboxamideYield 94%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound F (385 mg, 1.25 mmol) in 3:1 acetone/water (8 mL) was added N-oxide-4-methylmorpholine (220 mg, 1.87 mmol) and osmium tetroxide (254 μL, 0.025 mmol). After the reaction stirred for one hour, sodium periodate (294 mg, 1.37 mmol) was added. After another two hours, the reaction was diluted with EtOAc and washed well with a 10% NaS2O3 solution. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 365 mg (94%) of the title compound that was used without further purification. ES-MS [M+1]+: 311.2.

Workup

  1. waitAfter another two hours
  2. washwashed well with a 10% NaS2O3 solution
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f79fb1a4b2d1440fbc82ce826203753a
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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