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

HRID 1504163Notes

Reaction equation

HRID 1504163 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-e9ac0515c9a24803acff33f929a27123
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

Loading…