Iodoethane → HCID 13234027, compound

HRID 1632502Notes

Reaction equation

HRID 1632502 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([CH3:22])=[C:12]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].[CH2:23](I)[CH3:24]>CN(C)C=O.[H-].[Na+]>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([CH3:22])=[C:12]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[CH:13]=2)[N:8]([CH2:23][CH3:24])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 13234019HCID 13234019, compound

Product 1

HCID 13234027HCID 13234027, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24758Sodium hydrideSolvent

Procedure

30 g of 6-butyryl-7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester are dissolved in 1000 ml of dimethylformamide and, in the course of one hour, 4.8 g of a 50% strength sodium hydride dispersion in mineral oil are added in portions. Stirring is carried out for 1 hour at room temperature and then 31.2 g of ethyl iodide are added, and the mixture is then stirred at room temperature for 1 hour, concentrated under reduced pressure, cooled with ice-water and filtered with suction. The product obtained by filtering with suction is dissolved in ethyl acetate, washed with water, dried over sodium sulphate, concentrated and cooled in an ice bath. The precipitated crystallisate is filtered with suction and recrystallised from ethyl acetate. 1-Ethyl-6-butyryl-7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester having a melting point of 145°-146° is obtained.

Workup

  1. additionare added in portions
  2. stirringthe mixture is then stirred at room temperature for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. temperaturecooled with ice-water
  5. filtrationfiltered with suction
  6. customThe product obtained
  7. filtrationby filtering with suction
  8. dissolutionis dissolved in ethyl acetate
  9. washwashed with water
  10. dry with materialdried over sodium sulphate
  11. concentrationconcentrated
  12. temperaturecooled in an ice bath
  13. filtrationThe precipitated crystallisate is filtered with suction
  14. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-95d761d0612c4a02bec7b2e0e6405313
Source dataset
uspto-grants-1984_10
Patent number
US04476132

Reaction notes

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