Water → 6-(8-Bromooctyloxy)-2-methoxyquinoline

HRID 1504164

Reaction equation

HRID 1504164 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:14][CH3:15])[CH:8]=[CH:7]2.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br.O>CN(C=O)C>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([O:14][CH3:15])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 783101,8-DibromooctaneHCID 450911926-Hydroxy-2-methoxyquinoline

Product 1

HCID 669608866-(8-Bromooctyloxy)-2-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% in oil, 40 mg) was suspended in DMF(2 ml), and was cooled to 0° C. in ice water bath. 6-Hydroxy-2-methoxyquinoline(171 mg) was added thereto at the same temperature, and the mixture was stirred at 0° C. for an hour. 1,8-Dibromooctane(0.37 ml) was added thereto, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried with sodium sulfate, and was condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=10:1). The purified product was condensed to dryness under reduced pressure to give the title compound(225 mg) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionfollowed by extraction
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. customcondensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=10:1)
  6. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-09b94b0f72544cd19447b4e57e184c4d
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Linked notes

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