Potassium Iodide → HCID 117776656, compound

HRID 1477458Notes

Reaction equation

HRID 1477458 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:13]([O:15]CC)=[O:14].[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+].Cl[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1>CN(C=O)C.O.C(OCC)(=O)C>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[CH:4]=[C:3]([C:13]([OH:15])=[O:14])[C:2]2=[O:1]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 971603-Quinolinecarboxylic acid, 8-chloro-4-hydroxy-, ethyl ester

Product 1

HCID 117776656HCID 117776656, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 4-oxo-8-chloro-1,4-dihydroquinoline-3-carboxylate (1.0 g), potassium iodide (0.66 g) and sodium carbonate (1.1 g) in DMF (20 mL) was added 1-(chloromethyl)-4-methoxybenzene (0.7 mL), and the mixture was stirred at 70° C. overnight. The reaction mixture was diluted with water and ethyl acetate, and the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was solidified with a diisopropyl ether-ethyl acetate mixed solution. The obtained solid was dissolved in ethanol-THF (1:1, 12 mL), 1 N aqueous sodium hydroxide solution (6 mL) was added, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was diluted with water, neutralized with 1 N hydrochloric acid (10 mL), and the precipitate was collected by filtration, washed with water, and dried to give the title compound (0.52 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe obtained solid was dissolved in ethanol-THF (1:1, 12 mL)
  6. addition1 N aqueous sodium hydroxide solution (6 mL) was added
  7. stirringthe mixture was stirred at room temperature for 6 hr
  8. additionThe reaction mixture was diluted with water
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-b2a805c5de974b668111e45ae40ed4e2
Source dataset
uspto-grants-2016_08
Patent number
US09403802B2

Reaction notes

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