Phenol → HCID 19592863, compound

HRID 613571Notes

Reaction equation

HRID 613571 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[C:20]2[C:15](=[C:16]([NH:21][C:22](=[O:31])[C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:30])[CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[CH3:32]>CN1CCCC1=O>[Cl:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([Cl:29])[C:23]=1[C:22]([NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[N:14]=[CH:13][C:12]([CH3:32])=[C:11]2[O:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:31]

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 19592456HCID 19592456, compound

Product 1

HCID 19592863HCID 19592863, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of sodium hydride (60% in oil, 28.9 mg) and N-methylpyrrolidone (3 ml) was added phenol (113 mg) under ice-cooling, and the mixture was stirred for 30 minutes. To the mixture was added 4-chloro-8-(2,6-dichlorobenzoylamino)-3-methylquinoline (200 mg), and the mixture was stirred for 30 minutes at ambient temperature and for 4.5 hours at 120° C. The mixture was extracted with ethyl acetate, and the extract was washed with water, 1N sodium hydroxide solution and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized from ethanol to give 8-(2,6-dichlorobenzoylamino)-3-methyl-4-phenoxyquinoline (170 mg) as white crystal.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes at ambient temperature and for 4.5 hours at 120° C
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with water, 1N sodium hydroxide solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-da71a56e9982470490bf128bbe3f4c6c
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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