Sodium hydride → HCID 12926661, compound

HRID 1449383Notes

Reaction equation

HRID 1449383 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH:5]=1)[CH3:2].[H-].[Na+].[CH3:17]C(N(C)C)=O>>[CH3:17][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]1=[O:14]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 11063193HCID 11063193, compound

Product 1

HCID 12926661HCID 12926661, compound

Procedure

To a suspension of 1.9 g. of 4-ethoxyquinolin-2(1H)-one in 40 ml. of dimethylacetamide is added 0.42 g. of sodium hydride (56% in mineral oil, pentane washed), and the resulting mixture is heated at 60° C. for one hour. The mixture is filtered (while excluding moisture), cooled and there is then added 1.5 g. of methyliodide followed by stirring for 2 hours at ambient temperatures. The resulting mixture is poured into 200 ml. of cold water and the resulting slurry extracted 3 times each with 100 ml. of ethyl acetate. The combined organic extracts are washed with water and saturated sodium chloride solution, dried and evaporated in vacuo. The residue is crystallized from ether to obtain 1-methyl-4-ethoxyquinolin-2(1H)-one, m.p. 80°-82° C.

Workup

  1. additionTo a suspension of 1.9 g
  2. filtrationThe mixture is filtered (while excluding moisture)
  3. temperaturecooled
  4. additionthere is then added 1.5 g
  5. additionThe resulting mixture is poured into 200 ml
  6. extractionof cold water and the resulting slurry extracted 3 times each with 100 ml
  7. washThe combined organic extracts are washed with water and saturated sodium chloride solution
  8. customdried
  9. customevaporated in vacuo
  10. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-5c8e991dbbe54a79849cc15152fbd3ad
Source dataset
uspto-grants-1980_02
Patent number
US04190659

Reaction notes

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