Triethylsilane → HCID 52904958, compound

HRID 1801627Notes

Reaction equation

HRID 1801627 reaction equation
C([SiH](CC)CC)C.[CH3:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([CH:21]=O)[C:16](=[O:20])[NH:17]2)=[CH:12][CH:11]=1>FC(F)(F)C(O)=O>[CH3:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([CH3:21])[C:16](=[O:20])[NH:17]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 6002622-hydroxy-7-methoxyquinoline-3-carbaldehyde

Product 1

HCID 52904958HCID 52904958, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

30.7 ml of triethylsilane was added to a trifluoroacetic acid (300 ml) solution of 13 g of 7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde while being stirred under ice-cooling and stirred at room temperature overnight. The reaction solution was poured into ice water and extracted with dichloromethane and, after washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1), and 11.1 g of 7-methoxy-3-methyl-1H-quinolin-2-one was obtained in the form of a white powder.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature overnight
  3. extractionextracted with dichloromethane
  4. washafter washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-d1a6c6f0823b4e68bf399d6533b3646b
Source dataset
uspto-grants-2013_01
Patent number
US08349840B2

Reaction notes

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