Sodium Hydroxide → 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol

HRID 341830Notes

Reaction equation

HRID 341830 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([O:21]C(C56C(C)(C)C(C)(CC5)C(=O)O6)=O)[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([OH:21])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 676919055,6-dihydro-2-(2-phenylethyl)-6-((-)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyloxy)-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 98604535,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A portion (2.7 g) of the less polar fraction of 5,6-dihydro-2-(2-phenylethyl)-6-((-)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyloxy)-4H-imidazo[4,5,1-ij]quinoline obtained in Step 1 was dissolved in methanol (200 mL), followed by the addition of 2N aqueous sodium hydroxide (60 mL) and subsequent stirring at room temperature for 2 hrs; thereafter, the mixture was concentrated under reduced pressure and, to the residue was added water followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, then the solvents was removed under reduced pressure, and the residue was recrystallized from acetone-hexane to yield the titled (+)-5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol (1.2 g). The more polar fraction (3.7 g) was similarly treated to yield the titled (-)-5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-ol (1.7 g).

Workup

  1. concentrationthereafter, the mixture was concentrated under reduced pressure and, to the residue
  2. additionwas added water
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvents was removed under reduced pressure
  7. customthe residue was recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-52436755db3947c7a8d8147c76a0bec7
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

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