Sodium Hydroxide → 8-Hydroxyquinoline

HRID 1249644Notes

Reaction equation

HRID 1249644 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2S([O-])(=O)=O)[CH:4]=[CH:3][CH:2]=1.[Na+].[OH-:16].[Na+]>O>[OH:16][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23669146Sodium quinoline-8-sulfonate

Product 1

HCID 19238-HydroxyquinolineYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium quinoline-8-sulfonate (231 g) was added to 170 g of a 50% aqueous solution of sodium hydroxide, and the mixture was stirred. Then, 900 g of a hydrogenated triphenyl mixture was mixed, and the mixture was dehydrated. The dehydrated mixture was reacted at 260° C. for 15 minutes in a nitrogen stream. After cooling, 600 ml of water was added to the reaction mixture to separate the reaction medium layer. The aqueous layer was decolorized with activated carbon, acidified and then extracted with 200 ml of chloroform. The chloroform was recovered to give 140.9 g (yield 97.2%) of 8-hydroxyquinoline.

Workup

  1. customThe dehydrated mixture was reacted at 260° C. for 15 minutes in a nitrogen stream
  2. temperatureAfter cooling
  3. customto separate the reaction medium layer
  4. extractionextracted with 200 ml of chloroform
  5. customThe chloroform was recovered

Sources & evidence

ORD record
ord-598777ab442c45c7ac24497548efd2a9
Source dataset
uspto-grants-1986_12
Patent number
US04633024

Reaction notes

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