1,4-Dibromobutane → 7-(4-Bromobutoxy)-quinoline-2(1H)-one

HRID 1750080ノート

反応式

HRID 1750080 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 109757877-Hydroxycarbostyril

生成物 1

HCID 107563157-(4-Bromobutoxy)-quinoline-2(1H)-one収率 41.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of intermediate 14 (193 mg, 1.2 mmol), 1,4-dibromobutane (0.43 mL, 3.6 mmol) and anhydrous K2CO3 (166 mg, 1.2 mmol) was dissolved in EtOH and the solution was heated to reflux overnight. The solution was diluted with water and extracted with EtOAc. The combined organic layers was washed with saturated aq NaHCO3, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc=2:1) to give 7-(4-bromobutoxy)quinolin-2(1H)-one (intermediate 15) (147 mg, 41%) as a yellow solid.

後処理

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. extractionextracted with EtOAc
  4. washThe combined organic layers was washed with saturated aq NaHCO3, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel column (elution with PE/EtOAc=2:1)

出典と根拠

ORDレコード
ord-7a34e85f0b0448efa2fd470319653a82
出典データセット
uspto-grants-2015_10
特許番号
US09156822B2

反応ノート

読み込み中…