Trifluoroacetic acid → HCID 15260981, compound

HRID 1045665Notes

Reaction equation

HRID 1045665 reaction equation
[CH2:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH2:7][CH2:6][C:5]=2[NH:4][C:3](=[O:15])[CH2:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]1[C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[NH:4][C:3](=[O:15])[CH2:2]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 3226152,4,5,6-tetrahydro-1H-benzo[f]quinolin-3-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 15260981HCID 15260981, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,4,5,6-tetrahydro-2H-benzo[f]quinolin-3-one (10 g, 50.2 mmol) and triethylsilane (17.5 g, 150 mmol) in dichloromethane (100 ml) was stirred for 10 minutes. Trifluoroacetic acid (69 g, 605 mmol) was added dropwise with stirring and the mixture was stirred for 8 hours at room temperature. The mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with chloroform. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with ethyl acetate, and dried to afford (4aRS,10bSR)-trans-1,4,4a,5,6,10b-hexahydro-2H-benzo[f]quinolin-3-one (7.94 g, 39.5 mmol, 79%) as white crystals.

Workup

  1. stirringwith stirring
  2. stirringthe mixture was stirred for 8 hours at room temperature
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-46086f14e8d54224b26042fe6181af60
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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