Trifluoroacetic acid → HCID 21480570, compound

HRID 1490156Notes

Reaction equation

HRID 1490156 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]([CH3:21])[CH2:13][C:12]=3[CH2:11]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[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]([CH3:21])[C:15](=[O:20])[NH:16]3)[CH2:11]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21480568HCID 21480568, compound

Product 1

HCID 21480570HCID 21480570, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneSolvent

Procedure

3,4,5,6,7,8-Hexahydro-6-((4-methoxyphenyl)methyl)-3-methylquinolin-2[1H]-one (0.25 g) prepared according to Example 1, was suspended in triethylsilane (0.5 ml) and trifluoroacetic acid (0.5 ml) was added. The mixture was stirred for 30 minutes and then evaporated under reduced pressure. The residue was dissolved in chloroform and washed with saturated sodium carbonate solution and then with brine. The organic solution was dried (MgSO4) and evaporated to give the crude product (0.28 g), which was combined with a further batch 0.38 g. The crude product was purified by crystallisation from ethyl acetate/cyclohexane to give the title compound (0.2 g) m.p. 180°-208° C.

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with saturated sodium carbonate solution
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customevaporated
  6. customto give the crude product (0.28 g), which
  7. customThe crude product was purified by crystallisation from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-329cc1fae35d430a81f1f88c1de019a1
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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