2-Methoxyethanol → HCID 19592889, compound

HRID 613558Notes

Reaction equation

HRID 613558 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].CC(C)([O-])C.[K+].Cl[C:13]1[C:22]2[C:17](=[C:18]([NH:23][C:24](=[O:33])[C:25]3[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:32])[CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1>CN1CCCC1=O.C(OCC)(=O)C>[Cl:32][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([Cl:31])[C:25]=1[C:24]([NH:23][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:17]=1[N:16]=[CH:15][CH:14]=[C:13]2[O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:33]

Participants

6

Reactant 3

HCID 80192-MethoxyethanolHCID 195925644-Chloro-8-(2,6-dichlorobenzoylamino)quinolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 19592889HCID 19592889, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 2-methoxyethanol (130 mg) in N-methylpyrrolidone (2 ml) was added potassium tert-butoxide (172 mg) under ice-cooling, and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added 4-chloro-8-(2,6-dichlorobenzoylamino)quinoline (200 mg), and the mixture was stirred for 5 hours at 80° C. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethanol to give 8-(2,6-dichlorobenzoylamino)-4-(2-methoxyethoxy)quinoline (175 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 5 hours at 80° C
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-09792b71ad06463c85252fa709a73606
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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