Water → 6-(5-bromopentyloxy)-1-methyl-1H-quinolin-2-one

HRID 68992Notes

Reaction equation

HRID 68992 reaction equation
[H-].[Na+].[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[CH:14]=[CH:13]2.[CH3:21]I.O>CN(C=O)C>[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:21])[C:15](=[O:20])[CH:14]=[CH:13]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 669612306-(5-Bromopentyloxy)-1H-quinolin-2-one

Product 1

HCID 669600336-(5-bromopentyloxy)-1-methyl-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% in oil, 440 mg) was suspended in DMF (20 ml), and was cooled to 0° C. in ice water bath. 6-(5-Bromopentyloxy)-1H-quinolin-2-one (3.1 g) was added thereto at the same temperature, and the mixture was stirred at 0° C. for an hour. Methyl iodide (1.9 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=4:1→1:1). The purified product was condensed to dryness under reduced pressure to give the title compound (2.68 g) as a yellow 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=4:1→1:1)
  6. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-a7286fe3779f4bec8b91be40628a7295
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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