Iodoethane → HCID 12733857, compound

HRID 1578271Notes

Reaction equation

HRID 1578271 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[CH:7][C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]2[OH:18].C(=O)([O-])[O-].[K+].[K+].[CH2:25](I)[CH3:26]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]([CH2:25][CH3:26])[CH:7]=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]2=[O:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469564HCID 178469564, compound

Product 1

HCID 12733857HCID 12733857, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

33 g of the above compound were added to 50 cm3 of Dowtherm, heated at 250° C. and stirred in a round-bottomed flask equipped with a descending condenser which enabled the alcohol formed in the reaction to be collected; the reaction was complete after heating for 15 minutes. After cooling, the contents of the round-bottomed flask were taken up in 200 m3 of ethyl acetate. The solid was separated and recrystallised from dimethylformamide. 27.9 g of 6-bromo-7-chloro-3-ethoxycarbonyl-4-hydroxy-quinoline, m.p. 368°-370° C. (decomposition), were obtained. 13 g of 6-bromo-7-chloro-3-ethoxycarbonyl-4-hydroxyquinoline, 11 g of potassium carbonate and 100 cm3 of dimethylformamide were heated at 110° C. for 1 hour, whilst stirring. After cooling to 80° C., 16 cm3 of ethyl iodide were added to the mixture which was stirred and heated at 110° C. for 4 hours. After concentration to dryness in vacuo, the residue was taken up in 200 cm3 of water. The mixture was extracted with chloroform (3×100 cm3), and the combined organic extracts were washed with water, dried (MgSO4) and concentrated to dryness. The residue, recrystallised from 95 cm3 of isopropanol, gave 10 g of 6-bromo-7-chloro-1-ethyl-4-oxo-1,4-dihydro-3-ethoxycarbonylquinoline, m.p. 166° C. 10 g of the above ester were added to an aqueous-alcoholic solution of sodium hydroxide (NaOH:2.25 g, water:50 cm3, ethanol:100 cm3). The mixture was heated under reflux for 30 minutes. The solution was concentrated to dryness in vacuo. The residue was suspended in 100 cm3 of water. The solution was acidified by adding 3.4 cm3 of acetic acid. The solid was separated and recrystallised from DMF (90 cm3). 8.1 g (89%) of 6-bromo-7-chloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 320° C. (decomposition), were obtained.

Workup

  1. stirringwas stirred
  2. temperatureheated at 110° C. for 4 hours
  3. concentrationAfter concentration to dryness in vacuo
  4. extractionThe mixture was extracted with chloroform (3×100 cm3)
  5. washthe combined organic extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to dryness
  8. customThe residue, recrystallised from 95 cm3 of isopropanol

Sources & evidence

ORD record
ord-9242620163e74565bd0e4517be5907b9
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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