Sodium Hydroxide → HCID 22254517、化合物

HRID 434005

反応式

HRID 434005 の反応式
[N:1]1([CH:14]([CH2:17][CH3:18])[CH2:15][OH:16])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.Br[C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:21]=1[CH3:28].[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[N:1]1([CH:14]([CH2:17][CH3:18])[CH2:15][O:16][CH2:28][C:21]2[CH:20]=[CH:25][C:24]([C:26]#[N:27])=[CH:23][CH:22]=2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 140048403-Bromo-4-methylbenzonitrileHCID 21898023HCID 21898023、化合物

生成物 1

HCID 22254517HCID 22254517、化合物収率 60.2%

試薬・触媒・溶媒 3

HCID 5963Benzyltrimethylammonium chloride触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

2-(1H-imidazo[4,5-c]quinolin-1-yl)-1-butanol (3.0 g, 12.4 mmol) was added to a stirring mixture of cc-bromo-p-tolunitrile (3.0 g, 15.3 mmol), sodium hydroxide (40 ml, 50%), dichloromethane (40 ml), and benzyltrimethylammonium chloride (0.02 g, 0.11 mmol). The reaction was maintained for 72 hours and then diluted with dichloromethane (100 ml) and water (100 ml). The phases were separated and the aqueous phase was extracted with additional dichloromethane (100 ml). The organic fractions were combined, washed with water, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol, Rf0.48) to provide 2.66 g of 4-{[2-(1H-imidazo[4,5-c]quinolin-1-yl)butoxy]methyl}benzonitrile.

後処理

  1. temperatureThe reaction was maintained for 72 hours
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with additional dichloromethane (100 ml)
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol, Rf0.48)

出典と根拠

ORDレコード
ord-e012e80795af4fd1b38d7c43054bad18
出典データセット
uspto-grants-2003_12
特許番号
US06670372B2

関連ノート

読み込み中…