8-Hydroxyquinoline → 8-Quinolyl acrylate

HRID 2295799Notes

Reaction equation

HRID 2295799 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>C1(C)C=CC=CC=1>[C:19]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)(=[O:22])[CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 1696138-Quinolyl acrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8-Hydroxyquinoline (58.0 g: 0.40 mole) was dissolved in a mixture of toluene (500 ml) and triethylamine (41.4 g; 0.41 mole). Acrylyl chloride (38.0 g; 0.42 mole) was added slowly, while stirring, the reaction temperature beting kept under 30° C. When the addition was complete the mixture was stirred for another 1 hour. The solution was then filtered and washed with a solution of sodium hydrogen carbonate in water followed by water only, and finally the toluene layer was dried with anhydrous sodium sulphate. Some toluene was evaporated off using a rotary evaporator under low pressure. The solution was left in a refrigerator overnight and the solid formed was filtered off. This was identified by infra-red and N.M.R. spectroscopy and microanalysis to be 8-quinolinyl acrylate. Yield 48.6 g (61 percent of the theoretical yield).

Workup

  1. custombeting kept under 30° C
  2. additionWhen the addition
  3. stirringwas stirred for another 1 hour
  4. filtrationThe solution was then filtered
  5. washwashed with a solution of sodium hydrogen carbonate in water
  6. dry with materialfinally the toluene layer was dried with anhydrous sodium sulphate
  7. customSome toluene was evaporated off
  8. customa rotary evaporator under low pressure
  9. customthe solid formed
  10. filtrationwas filtered off
  11. customYield 48.6 g (61 percent of the theoretical yield)

Sources & evidence

ORD record
ord-8dd3bdb446d74bf18c2ee8f8ed872ba7
Source dataset
uspto-grants-1984_01
Patent number
US04426464

Reaction notes

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