Iodoethane → HCID 15675258, compound

HRID 1090136Notes

Reaction equation

HRID 1090136 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:14])[CH:9]=[CH:10][NH:11]2)=[CH:6][C:5]=1[O:15][CH3:16])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24]>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:14])[CH:9]=[CH:10][N:11]2[CH2:23][CH3:24])=[CH:6][C:5]=1[O:15][CH3:16])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 15675257HCID 15675257, compound2×

Product 1

HCID 15675258HCID 15675258, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Ethoxy-6-methoxy-4(1H)-quinolone (compound 62, 0.68 g) was dissolved in dimethylformamide (14 ml). Potassium carbonate (640 mg) and ethyl iodide (0.3 ml) were added to the solution, and the mixture was stirred at room temperature for 4 hours. The precipitate was removed by filtration, and the filtrate was purified by silica gel column chromatography (Wako Gel C-200, 50 g). Elution with a mixed solvent of chloroform (90 parts) and methanol (10 parts) gave 7-ethoxy-1-ethyl-6-methoxy-4(1H)-quinolone (compound 58, 0.4 g).

Workup

  1. customThe precipitate was removed by filtration
  2. customthe filtrate was purified by silica gel column chromatography (Wako Gel C-200, 50 g)
  3. washElution with a mixed solvent of chloroform (90 parts) and methanol (10 parts)

Sources & evidence

ORD record
ord-3092b43f64dd46d8a813d9196fc501b4
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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