Water → HCID 59216604, compound

HRID 2245296Notes

Reaction equation

HRID 2245296 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH:5]([OH:13])[C:6](=O)[NH:7]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.O>C1COCC1>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH:5]([OH:13])[CH2:6][NH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 59216597HCID 59216597, compound

Product 1

HCID 59216604HCID 59216604, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Amino-3-hydroxy-3,4-dihydroquinolin-2(1H)-one (300 mg, 1.68 mmol) is dissolved in THF (10 ml) and slowly added to a refluxing mixture of LiAlH4 (319 mg, 8.42 mmol) in 8 ml THF under an argon atmosphere. After 30 min refluxing the mixture is cooled to room temperature, ethyl acetate (10 ml) is added cautiously, thereafter water is added slowly and cautiously until a light grey precipitate formed. The solvent is collected and the precipitate is washed several times with ethyl acetate, the combined organic extracts are washed with water, dried over magnesium sulfate, filtered and evaporated to dryness. The crude material is purified by column chromatography (eluent: ethyl acetate). Yield: 182 mg (65%/).

Workup

  1. temperatureAfter 30 min refluxing the mixture
  2. customformed
  3. customThe solvent is collected
  4. washthe precipitate is washed several times with ethyl acetate
  5. washthe combined organic extracts are washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe crude material is purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-901766c3da9c4015bbc65f2091c113ae
Source dataset
uspto-grants-2010_03
Patent number
US07683076B2

Reaction notes

Loading…