Pyridine → HCID 19981549, compound

HRID 1461118Notes

Reaction equation

HRID 1461118 reaction equation
[C:1]([O:9][CH2:10][C:11](Cl)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19].N1C=CC=CC=1>CC(C)=O>[C:1]([O:9][CH2:10][C:11]([N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 120252-PyrrolidoneHCID 10888895Acetyl chloride, (benzoyloxy)-

Product 1

HCID 19981549HCID 19981549, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (benzoyloxy)acetyl chloride (1.98 g, 0.01 mole), pyrrolidone (0.85 g, 0.01 mole) and pyridine (0.8 g, 0.01 mole) in acetone (10 ml) was refluxed for 3 h. The cooled mixture was filtered and evaporated in vacuo. The residue was dissolved in ethyl acetate (50 ml) and the solution washed with a 2% aqueous solution of sodium bicarbonate, 2M hydrochloric acid and water. After drying over anhydrous sulphate, the organic phase was evaporated under reduced pressure to give a residue which crystallized by addition of ether. Recrystallization from ether-petroleum ether yielded 1.6 g (65%) of the title compound. Mp 83°-84° C.

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationThe cooled mixture was filtered
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  5. washthe solution washed with a 2% aqueous solution of sodium bicarbonate, 2M hydrochloric acid and water
  6. dry with materialAfter drying over anhydrous sulphate
  7. customthe organic phase was evaporated under reduced pressure
  8. customto give a residue which
  9. customcrystallized by addition of ether
  10. customRecrystallization from ether-petroleum ether

Sources & evidence

ORD record
ord-3e8437e1cff34a0e9b4b66914c8c664a
Source dataset
uspto-grants-1991_12
Patent number
US05073641

Reaction notes

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