Water → 5,6-dihydro-6-methoxy-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 341839Notes

Reaction equation

HRID 341839 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][C:11]2[N:21]3[C:22]4[C:17]([CH:18]([OH:23])[CH2:19][CH2:20]3)=[CH:16][CH:15]=[CH:14][C:13]=4[N:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:24]I.O>O1CCCC1>[CH3:24][O:23][CH:18]1[C:17]2[C:22]3=[C:13]([N:12]=[C:11]([CH2:10][CH2:9][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[N:21]3[CH2:20][CH2:19]1)[CH:14]=[CH:15][CH:16]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 98604535,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol

Product 1

HCID 158384685,6-dihydro-6-methoxy-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolineYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A portion (115 mg) of 60% sodium hydride was added to anhydrous tetrahydrofuran (15 mL) under an argon atmosphere; 0.2 g of 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol obtained in Example 4 was dissolved in anhydrous tetrahydrofuran (4 mL) and the solution was added dropwise to the first mentioned solution at room temperature. After stirring for 35 min at room temperature, methyl iodide (1.02 g) was added dropwise and the mixture was stirred for 4 hrs. Water was added to the reaction solution and the mixture was stirred; thereafter, the reaction solution was extracted with dichloromethane, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to yield the titled compound as a yellow oil (103 mg).

Workup

  1. additionthe solution was added dropwise to the
  2. customat room temperature
  3. stirringthe mixture was stirred for 4 hrs
  4. stirringthe mixture was stirred
  5. extractionthereafter, the reaction solution was extracted with dichloromethane
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1cf4f09a45d64ca1861103abf45f5aa5
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

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