Iodoethane → HCID 54482604, compound

HRID 1632504Notes

Reaction equation

HRID 1632504 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][C:11]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])=[C:10]([CH3:22])[CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[CH2:25](I)[CH3:26]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH2:25][CH3:26])[C:13]2[C:8](=[CH:9][C:10]([CH3:22])=[C:11]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13234021HCID 13234021, compound

Product 1

HCID 54482604HCID 54482604, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.3 g of 6-Butyryl-7-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid ethyl ester are dissolved in 330 ml of dimethylformamide, and 2.6 g of a 50% strength sodium hydride dispersion in mineral oil are added. Stirring is carried out overnight at room temperature and then 8.7 ml of ethyl iodide are added dropwise, and the mixture is stirred for 2 hours at room temperature, concentrated under reduced pressure at 60°, poured onto ice, acidified and filtered with suction. 4-Ethoxy-6-butyryl-7-methylquinoline-2-carboxylic acid ethyl ester having a melting point of 123°-124° is obtained.

Workup

  1. stirringthe mixture is stirred for 2 hours at room temperature
  2. concentrationconcentrated under reduced pressure at 60°
  3. additionpoured onto ice
  4. filtrationfiltered with suction

Sources & evidence

ORD record
ord-1aab45e142644ab2bac3d6ff70d96797
Source dataset
uspto-grants-1984_10
Patent number
US04476132

Reaction notes

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