Iodoethane → HCID 12733873, compound

HRID 544234Notes

Reaction equation

HRID 544234 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([Cl:18])=[C:12]([Br:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])C.C(=O)([O-])[O-].[CH2:23](I)[CH3:24]>CN(C=O)C>[Br:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[Cl:18])[N:8]([CH2:23][CH3:24])[CH:7]=[C:6]([C:4]([OH:3])=[O:5])[C:15]2=[O:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 19660Carbonate IonHCID 12733848HCID 12733848, compound

Product 1

HCID 12733873HCID 12733873, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the above ester (7.5 g), pottasium carbonate (7.8 g), ethyl iodide (9.0 ml) and DMF (100 ml was stirred at 90°-110° C. for 10 hours and evaporated. The residue was extracted with chloroform, the chloroform layer was washed with water, and dried. The solvent was evaporated. The residue was added to a solution of sodium hydroxide (4.2 g) and water (100 ml) and refluxed for 30 minutes. The alkaline solution was acidified with concentrated hydrochloric acid and the precipitate was filtered. The precipitate was washed with water, dried, and recrystallized from DMF to give 6-bromo-7-chloro-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (6.9 g).

Workup

  1. customevaporated
  2. extractionThe residue was extracted with chloroform
  3. washthe chloroform layer was washed with water
  4. customdried
  5. customThe solvent was evaporated
  6. additionThe residue was added to a solution of sodium hydroxide (4.2 g) and water (100 ml)
  7. temperaturerefluxed for 30 minutes
  8. filtrationthe precipitate was filtered
  9. washThe precipitate was washed with water
  10. customdried
  11. customrecrystallized from DMF

Sources & evidence

ORD record
ord-f0dd6c07c8f4473fbffa2884dc5caa12
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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