Iodoethane → HCID 11063193, compound

HRID 1680538Notes

Reaction equation

HRID 1680538 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][C:2]1=[O:12].[H-].[Na+].[CH2:15](I)[CH3:16]>CC(N(C)C)=O>[CH2:15]([O:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:1][C:2](=[O:12])[CH:3]=1)[CH3:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 3677260Quinoline-2,4(1H,3H)-dione

Product 1

HCID 11063193HCID 11063193, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a suspension of 6 g. of quinoline-2,4-dione in 50 ml. of dimethylacetamide is added 1.6 g. of sodium hydride (56% in mineral oil, pentane washed). The mixture is then stirred at room temperature for 90 minutes and 6 g. of ethyliodide is added and the resulting mixture is heated briefly at 35° C. followed by stirring at ambient temperature for 18 hours. The precipitate which forms is recovered by filtering and the filtrate is poured into 200 ml. of water and the resulting precipitate also recovered by filtering and dried. The two filter cakes above obtained are combined and crystallized from methanol to obtain 4-ethoxyquinolin-2(1H)-one, m.p. 223°-226° C.

Workup

  1. additionTo a suspension of 6 g
  2. temperaturethe resulting mixture is heated briefly at 35° C.
  3. stirringby stirring at ambient temperature for 18 hours
  4. customThe precipitate which forms is recovered
  5. filtrationby filtering
  6. additionthe filtrate is poured into 200 ml
  7. customof water and the resulting precipitate also recovered
  8. filtrationby filtering
  9. customdried
  10. filtrationThe two filter cakes
  11. customabove obtained
  12. customcrystallized from methanol

Sources & evidence

ORD record
ord-739742e9205a4425b407b801e8d0f603
Source dataset
uspto-grants-1981_06
Patent number
US04273930

Reaction notes

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