Ethyl Acetate → 5,6-dihydro-6-methylene-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 341834Notes

Reaction equation

HRID 341834 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[C:7]1([CH2:13][CH2:14][C:15]2[N:25]3[C:26]4C(C(=O)C[CH2:24]3)=[CH:20][CH:19]=[CH:18][C:17]=4[N:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:1]=[C:2]1[C:5]2[C:26]3=[C:17]([N:16]=[C:15]([CH2:14][CH2:13][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:25]3[CH2:24][CH2:3]1)[CH:18]=[CH:19][CH:20]=2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 158384624,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]-quinolin-6-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 158384645,6-dihydro-6-methylene-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolineYield 82.6%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

Methyltriphenylphosphonium bromide (1.29 g) was suspended in anhydrous tetrahydrofuran (10 mL) and a solution of potassium t-butoxide (0.45 g) in tetrahydrofuran (10 mL) was added dropwise at room temperature, followed by stirring for 1 hr at room temperature. Subsequently, 0.50 g of 4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one obtained in Example 1 was dissolved in anhydrous tetrahydrofuran (10 mL) and the solution was added dropwise and the mixture was stirred at room temperature for 1 hr. To the reaction solution, a saturated aqueous solution of sodium hydrogencarbonate (50 mL) and ethyl acetate (50 mL) were added and then two layers were separated. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/ethyl acetate) to yield the titled compound as colorless crystals (0.41 g).

Workup

  1. additionthe solution was added dropwise
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. customtwo layers were separated
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-8a1affed58ea4164b6e9fac1f1c4b42a
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

Loading…