Methanol → HCID 18796633, compound

HRID 1900698Notes

Reaction equation

HRID 1900698 reaction equation
Cl[C:2]1[CH:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([Cl:22])[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:23])[CH:8]=2)[N:3]=1.CO.C[C:27](C)([O-:29])C.[K+].O1CCOCC1>O>[CH3:27][O:29][C:2]1[CH:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([Cl:22])[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:23])[CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 312751,4-DioxaneHCID 18796724HCID 18796724, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18796633HCID 18796633, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 200 mg of 2,6-dichloro-4-(3-chloro-4-methoxybenzyl)aminoquinoline, 0.5 ml of methanol, 200 mg of potassium t-butoxide and 3 ml of 1,4-dioxane was heated under reflux for one hour and cooled, followed by the addition of water. The resulting mixture was extracted with ethyl acetate and the ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 10 to 30% ethyl acetate/hexane and recrystallized from ethyl acetate/hexane to give 150 mg of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. temperaturecooled
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography with 10 to 30% ethyl acetate/hexane
  9. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4b53a8ca6df44f6cb3b2fcfa77d34924
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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