Potassium Iodide → HCID 86732736, compound

HRID 525869Notes

Reaction equation

HRID 525869 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([OH:14])=[C:10]([OH:13])[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([O:18][CH3:19])=[O:17])=[N:4]1)[CH3:2].[C:20](=[O:23])([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1>CC(C)=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH2:6][C:7]3[CH:12]=[CH:11][C:10]([O:23][CH3:20])=[CH:9][CH:8]=3)=[C:10]([O:13][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([O:18][CH3:19])=[O:17])=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 136341437HCID 136341437, compound

Product 1

HCID 86732736HCID 86732736, compoundYield 137.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of methyl 1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydrocinnoline-3-carboxylate (11 g, 35.8 mmol), potassium carbonate (16.33 g, 118 mmol) and potassium iodide (1.189 g, 7.16 mmol) in acetone (200 mL) at room temperature, was added 1-(chloromethyl)-4-methoxybenzene (16.82 g, 107 mmol). The mixture was then heated to reflux overnight. After cooling to room temperature, the mixture was concentrated in vacuo and the residue was partitioned between dichloromethane and brine. The organic phase was separated, and the aqueous phase was extracted with dichloromethane several times. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by automatic silica gel column chromatography (Combiflash RF) eluting with methanol/dichloromethane (0-20%) to afford methyl 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylate (15 g, 24.68 mmol, 68.9% yield) as a light yellow solid. LCMS: (M+H)+: 505.1.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux overnight
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue was partitioned between dichloromethane and brine
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with dichloromethane several times
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by automatic silica gel column chromatography (Combiflash RF)
  11. washeluting with methanol/dichloromethane (0-20%)

Sources & evidence

ORD record
ord-5aff58366bf9426c994d4e2ebbe16841
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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