cis-Tetrahydropentalene-2,5(1H,3H)-dione → 8-Hydroxyquinoline

HRID 636285Notes

Reaction equation

HRID 636285 reaction equation
[CH:1]12[CH2:8][C:7](=O)[CH2:6][CH:5]1[CH2:4]C(=O)[CH2:2]2.Cl.[NH2:12]O.[CH3:14][C:15]([O-:17])=O.[Na+]>CO>[CH:2]1[CH:14]=[C:15]([OH:17])[C:4]2[N:12]=[CH:8][CH:7]=[CH:6][C:5]=2[CH:1]=1

Participants

5

Reactant 3

HCID 103526cis-Tetrahydropentalene-2,5(1H,3H)-dioneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 19238-HydroxyquinolineYield 60.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To bicyclo[3.3.0]octane-3,7-dione (0.25 g, 1.81 mmol) in dry MeOH (3 mL) at 0° C. was added hydroxylamine hydrochloride (0.28 g, 4.30 mmol) and NaOAc (0.65 g, 7.92 mmol). After 1 h, the solvent was removed under vacuum. Triturate the resulting residue with a minimum of ice-cold water to give a white precipitate. Collect and dry the precipitate under vacuum to give 0.16 g of the crude oxine.

Workup

  1. customthe solvent was removed under vacuum
  2. customTriturate the resulting residue with a minimum of ice-cold water
  3. customto give a white precipitate
  4. customCollect
  5. customdry the precipitate under vacuum

Sources & evidence

ORD record
ord-9f13c482ab3f400b8f12279ed98d9dee
Source dataset
uspto-grants-2001_02
Patent number
US06191146B1

Reaction notes

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