Trifluoroacetic acid → HCID 18967734, compound

HRID 1490160Notes

Reaction equation

HRID 1490160 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]2[CH2:19][CH2:18][C:17]3[NH:16][C:15](=[O:20])[CH:14]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][C:12]=3[CH2:11]2)=[CH:5][CH:4]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]2[CH2:19][CH2:18][CH:17]3[CH:12]([CH2:13][CH:14]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:15](=[O:20])[NH:16]3)[CH2:11]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 18967735HCID 18967735, compound

Product 1

HCID 18967734HCID 18967734, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Procedure

Ethyl 3,4,5,6,7,8-hexahydro-6-((4-methoxyphenyl)methylquinolin-2[1H]-one-3-carboxylate (0.35 g) (prepared as in Example 5) was dissolved in CH2 Cl2 (1 ml) and triethylsilane (1.5 ml) was added. The solution was cooled with ice. TFA (1.5 ml) was added and the mixture was left to stir 1.5 hours. The reaction mixture was evaporated under reduced pressure and the residue dissolved in chloroform. The chloroform solution was washed with saturated sodium carbonate solution, dried (MgSO4) and evaporated. The residue was suspended in ether, filtered and the solid obtained was recrystallised from ethyl acetate to give the title compound (0.14 g) mp 142°-144° C.

Workup

  1. temperatureThe solution was cooled with ice
  2. waitthe mixture was left
  3. customThe reaction mixture was evaporated under reduced pressure
  4. dissolutionthe residue dissolved in chloroform
  5. washThe chloroform solution was washed with saturated sodium carbonate solution
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. filtrationfiltered
  9. customthe solid obtained
  10. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-f9ad5ee442464d089d4678dad2fe2a11
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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