Iodoethane → HCID 12770912, compound

HRID 434567Notes

Reaction equation

HRID 434567 reaction equation
[CH2:1](N(CC)CC)[CH3:2].Cl.[CH2:9]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([F:28])=[C:18]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:19]=2[F:21])[C:14](=[O:29])[C:13]([C:30]([OH:32])=[O:31])=[CH:12]1)[CH3:10].C(I)C>CN(C=O)C>[CH2:9]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([F:28])=[C:18]([N:22]3[CH2:23][CH2:24][N:25]([CH2:1][CH3:2])[CH2:26][CH2:27]3)[C:19]=2[F:21])[C:14](=[O:29])[C:13]([C:30]([OH:32])=[O:31])=[CH:12]1)[CH3:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 12770893HCID 12770893, compound

Product 1

HCID 12770912HCID 12770912, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Triethylamine (0.2 g), 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid hydrochloride (0.3 g), ethyl iodide (0.19 g), and DMF (5 ml) were mixed, heated with stirring at 90° C. for 3 hours, and the solvent was evaporated. The residue was dissolved in 2N sodium hydroxide solution. The alkaline solution was neutralized with aqueous acetic acid and extracted with dichloromethane. The dichloromethane layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was recrystallized from a mixture of DMF and ethanol to give 1-ethyl-7-(4-ethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.06 g), mp 236°-239° C.

Workup

  1. temperatureheated
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in 2N sodium hydroxide solution
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe residue was recrystallized from a mixture of DMF and ethanol

Sources & evidence

ORD record
ord-b56fb3c055eb4d27b6b191baa5617f16
Source dataset
uspto-grants-1983_08
Patent number
US04398029

Reaction notes

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