Sodium Hydroxide → 8-Quinolinol, 5-benzyl-

HRID 1905387Notes

Reaction equation

HRID 1905387 reaction equation
[OH-].[Na+].O.NN.[C:6]([C:14]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[N:19]2)(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)CO>[C:7]1([CH2:6][C:14]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[N:19]3)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 2414928-Hydroxy-5-quinolyl phenyl ketone

Product 1

HCID 814038-Quinolinol, 5-benzyl-Yield 69.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a solution of 2.88 g (72 mmol, 5.5 eq.) of powdered sodium hydroxide and 6.55 ml (135 mmol, 10.3 eq.) of hydrazine monohydrate in 40 ml of ethylene glycol was added 3.08 g (13.1 mmol) of 5-benzoyl-8-quinolinol and the resultant mixture was heated at 120° C. for one hour. The reflux condenser was removed and heating was continued until the pot temperature had reached 195° C. The condenser was replaced and refluxing continued for an additional three hours. The solution was cooled, diluted with 120 ml of water and brought to pH 7 with 1M hydrochloric acid. After the addition of 100 ml of pH 6.5 lM phosphate buffer and 500 ml of ethyl acetate, the layers were separated. The organic phase was washed with 100 ml of pH 6.5 1M phosphate buffer, two 100 ml portions of water and 100 ml of brine, dried over sodium sulfate and evaporated to yield 3.64 g of a dark brown, viscous oil. Purification required flash chromatography on 200 g of silica, eluted with 5:95 methanol:dichloromethane followed by recrystallization from heptane to provide 2.14 g of yellow crystals:melting point 112°-113° C.

Workup

  1. customThe reflux condenser was removed
  2. temperatureheating
  3. customhad reached 195° C
  4. temperaturerefluxing
  5. temperatureThe solution was cooled
  6. additiondiluted with 120 ml of water
  7. additionAfter the addition of 100 ml of pH 6.5 lM phosphate buffer and 500 ml of ethyl acetate
  8. customthe layers were separated
  9. washThe organic phase was washed with 100 ml of pH 6.5 1M phosphate buffer, two 100 ml portions of water and 100 ml of brine
  10. dry with materialdried over sodium sulfate
  11. customevaporated
  12. customto yield 3.64 g of a dark brown, viscous oil
  13. customPurification required flash chromatography on 200 g of silica
  14. washeluted with 5:95 methanol
  15. customdichloromethane followed by recrystallization from heptane

Sources & evidence

ORD record
ord-a9b095c396234e0ba090f4fccd366aca
Source dataset
uspto-grants-1989_06
Patent number
US04843082

Reaction notes

Loading…