Triethylsilane → HCID 19593045, compound

HRID 613530Notes

Reaction equation

HRID 613530 reaction equation
O[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O.ClCCl>[CH3:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 19592820HCID 19592820, compound

Product 1

HCID 19593045HCID 19593045, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1,4-dihydro-3-hydroxymethyl-8-nitro-4-oxoquinoline (3.1 g) in trifluoroacetic acid (10 ml) and dichloromethane (10 ml) was added triethylsilane (6.55 g), and the mixture was stirred at ambient temperature overnight. The mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give 1,4-dihydro-3-methyl-8-nitro-4-oxoquinoline (2.3 g).

Workup

  1. customThe mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-754c0badb4ec4201aab3d322d5aa3111
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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