1,4-Dibromobutane → 2-Hydroxyquinoline

HRID 887059Notes

Reaction equation

HRID 887059 reaction equation
C(=O)([O-])[O-].[K+].[K+].O[C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1.BrCCCCBr>CN(C)C=O>[NH:15]1[C:16]2[C:11](=[CH:10][CH:9]=[CH:8][CH:17]=2)[CH:12]=[CH:13][C:14]1=[O:18]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 27857587-Hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 60382-Hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of anhydrous potassium carbonate (K2CO3) (10.50 g, 0.075 mol) in 100 mL of anhydrous N,N-dimethylformamide (DMF) was added 7-hydroxyquinolinone 1 (10.00 g, 0.06 mol) followed by 1,4-dibromobutane 2 (25.91 g, 0.12 mol). The resulting mixture was heated at 60° C. for 12 h. The progress of the reaction was monitored by thin layer chromatography (TLC) technique. After cooling to room temperature, the reaction mixture was filtered through a sintered funnel and the precipitate was washed with ethyl acetate (25 mL×2). The combined filtrate was concentrated on a rotavapor. The residue was diluted with 250 mL of ethyl acetate, washed with water (100 mL×2), dried over anhydrous magnesium sulfate and evaporated the solvent. The residue was triturated with hexane and then filtered the precipitate to give the pure title compound 3. White solid, 12.88 g (72%). 1H NMR (400 MHz, CDCl3): δ 1.92-1.97 (m, 2H); 2.05-2.10 (m, 2H); 2.64 (t, J=9.2 Hz, 2H); 2.92 (t, J=9.2 Hz, 2H); 3.50 (t, J=7.6 Hz, 2H); 3.98 (t, J=7.6 Hz, 2H); 6.37 (d, J=3.2 Hz, 1H); 6.50-6.54 (m, 1H); 7.04 (d, J=11.2 Hz, 1H), 8.61 (broad s, 1H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through a sintered funnel
  3. washthe precipitate was washed with ethyl acetate (25 mL×2)
  4. concentrationThe combined filtrate was concentrated on a rotavapor
  5. additionThe residue was diluted with 250 mL of ethyl acetate
  6. washwashed with water (100 mL×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated the solvent
  9. customThe residue was triturated with hexane
  10. filtrationfiltered the precipitate

Sources & evidence

ORD record
ord-d6305257a6eb4c7f8737b597a13e89f3
Source dataset
uspto-grants-2012_08
Patent number
US08247420B2

Reaction notes

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