Triethylsilane → ethyl 5,6-dihydro-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylate

HRID 1600625Notes

Reaction equation

HRID 1600625 reaction equation
C([SiH](CC)CC)C.[CH3:8][C:9]1[C:18]2[CH:19]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:16]3[C:17]=2[C:12]([C:13](=O)[CH2:14][CH2:15]3)=[CH:11][CH:10]=1>FC(F)(F)C(O)=O>[CH3:8][C:9]1[C:18]2[CH:19]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:16]3[C:17]=2[C:12]([CH2:13][CH2:14][CH2:15]3)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 15432798ethyl 5,6-dihydro-9-methyl-6-oxo-4H-pyrrolo [3,2,1-ij]quinoline-2-carboxylate

Product 1

HCID 21714341ethyl 5,6-dihydro-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylateYield 54.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (3.07 g, 26.4 mmol) was added dropwise to a mixture of ethyl 5,6-dihydro-9-methyl-6-oxo-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylate (1.70 g, 6.61 mmol) and trifluoroacetic acid (20 ml) at room temperature. Then, the reaction mixture was stirred at room temperature for 3 hours and distilled under reduced pressure to remove the solvent. Ice water was added to the residue, followed by extraction with ethyl acetate (twice). The extract solution was washed with a 5% aqueous sodium hydrogencarbonate solution and then a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/97) to obtain 0.87 g of ethyl 5,6-dihydro-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylate. M.p. 51-52° C. (after recrystallization from n-hexane).

Workup

  1. distillationdistilled under reduced pressure
  2. customto remove the solvent
  3. additionIce water was added to the residue
  4. extractionfollowed by extraction with ethyl acetate (twice)
  5. washThe extract solution was washed with a 5% aqueous sodium hydrogencarbonate solution
  6. dry with materiala 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/97)

Sources & evidence

ORD record
ord-103b7607a634434ab3ee098ffc093d33
Source dataset
uspto-grants-1999_11
Patent number
US05977100

Reaction notes

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