3-Hydroxyquinoline → HCID 70968042, compound

HRID 1618900Notes

Reaction equation

HRID 1618900 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Na+].F[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]#[N:18]>CN1CCCC1=O>[C:17]([C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)#[N:18]

Participants

5

Reactant 3

HCID 113763-HydroxyquinolineHCID 24758Sodium hydrideHCID 678552-Fluorobenzonitrile

Product 1

HCID 70968042HCID 70968042, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

After 0.27 g of 3-hydroxyquinoline was dissolved in N-methyl-2-pyrrolidone, 0.087 g of sodium hydride (60% oil dispersion) was added under ice-cooling, and the mixture was stirred for 30 minutes. At the same temperature, 0.27 g of 2-fluorobenzonitrile was added and then the mixture was stirred for 6 hours at room temperature. After the reaction mixture was poured into ice water, extracted with ethyl acetate, and washed with saturated saline solution, the resultant was dried with magnesium sulfate. After the solvent was evaporated under reduced pressure, the crude product was purified by silica gel column chromatography to obtain 0.37 g of 3-(2-cyanophenoxy)quinoline (Compound Number 62).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 6 hours at room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated saline solution
  5. dry with materialthe resultant was dried with magnesium sulfate
  6. customAfter the solvent was evaporated under reduced pressure
  7. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6225f4ca0ce94b83bd8aafe913086e01
Source dataset
uspto-grants-2014_07
Patent number
US08772200B2

Reaction notes

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