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

HRID 341828Notes

Reaction equation

HRID 341828 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([C:16](=[O: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.[BH4-].[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 4311764Sodium borohydrideHCID 158384624,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]-quinolin-6-one

Product 1

HCID 98604535,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-olYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Fourteen grams of 4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one obtained in Example 1 was dissolved in dry methanol (140 mL); following the addition of sodium borohydride (0.76 g) under ice cooling and subsequent stirring at room temperature for 1 hr, the solvent was removed under reduced pressure and water was added to the residue, followed by extraction with dichloromethane. The organic layers were combined, washed with water and saturated brine successively, and dried over anhydrous sodium sulfate; thereafter, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluting solution: hexane/ethyl acetate) to yield the titled compound as colorless crystals (13.3 g).

Workup

  1. customthe solvent was removed under reduced pressure and water
  2. additionwas added to the residue
  3. extractionfollowed by extraction with dichloromethane
  4. washwashed with water and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthereafter, the solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluting solution: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bbf2ba647b7b43ccb5f88d4e884f9a88
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

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