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Dimethylformamide → 7-Methoxy-4-(2-methyl-quinolin-3-yloxy)-6-oxiranylmethoxy-quinoline

HRID 229022
Notes
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Reaction equation

HRID 229022 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([O:18][C:19]3[C:20]([CH3:29])=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[OH:30].C(=O)([O-])[O-].[K+].[K+].[CH2:37]([CH:39]1[O:41][CH2:40]1)Br>O>[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([O:18][C:19]3[C:20]([CH3:29])=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:30][CH2:37][CH:39]1[CH2:40][O:41]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 230782657-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-6-ol

Product 1

HCID 230782567-Methoxy-4-(2-methyl-quinolin-3-yloxy)-6-oxiranylmethoxy-quinolineYield 27%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

N,N-Dimethylformamide (6 ml) was added to 7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-6-ol (189 mg), potassium carbonate (236 mg), and epibromohydrin (234 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using hexane-acetone to give 7-methoxy-4-(2-methyl-quinolin-3-yloxy)-6-oxiranylmethoxy-quinoline (59 mg, yield 27%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-0f340bb7ea3142eeba9878768e4efbe3
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes