Potassium Carbonate → 3,4-dihydro-3,3-dimethyl-6-methylthio-2(1H)-quinolinone

HRID 2268779Notes

Reaction equation

HRID 2268779 reaction equation
C([SiH](CC)CC)C.[CH3:8][C:9]1([CH3:23])[C:18](=O)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([S:20][CH3:21])[CH:16]=2)[NH:11][C:10]1=[O:22].C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[CH3:8][C:9]1([CH3:23])[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([S:20][CH3:21])[CH:16]=2)[NH:11][C:10]1=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 225957253,3-dimethyl-6-methylthio-2,4(1H,3H)-quinolinedione

Product 1

HCID 225957533,4-dihydro-3,3-dimethyl-6-methylthio-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (34.75 ml, 49.1 g, 0.042 mol) was added dropwise to a stirred solution of 3,3-dimethyl-6-methylthio-2,4(1H,3H)-quinolinedione (12.79 g, 0.054 mol) in trifluoroacetic acid (520 ml) under nitrogen at 60° C. The reaction was then allowed to cool slowly to room temperature and was stirred for 16 hr. The solvent was then evaporated in vacuo to afford a yellow residue. The residue was then poured into saturated potassium carbonate solution (200 ml). The product was extracted with ethyl acetate (3×150 ml) The organic extracts were combined, washed with water (200 ml), dried and concentrated in vacuo to afford 3,4-dihydro-3,3-dimethyl-6-methylthio-2(1H)-quinolinone as a yellow solid. Mp 154° C.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customto afford a yellow residue
  3. extractionThe product was extracted with ethyl acetate (3×150 ml) The organic extracts
  4. washwashed with water (200 ml)
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d38fb28dce82400da8f752504effd6f3
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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