Methanol → 1-(1-{[(3-chlorobenzyl)oxy]methyl}propyl)-1H-imidazo[4,5-c]quinoline

HRID 433976

反応式

HRID 433976 の反応式
[CH2:1]([CH:3]([N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=[CH:7]1)[CH2:4][OH:5])[CH3:2].[OH-].[Na+].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br.CO>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][O:5][CH2:4][CH:3]([N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=[CH:7]1)[CH2:1][CH3:2]

参加物

8

反応物 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 218980232-(1H-imidazo[4,5-c]quinolin-1-yl)-1-butanol

生成物 1

HCID 222545191-(1-{[(3-chlorobenzyl)oxy]methyl}propyl)-1H-imidazo[4,5-c]quinoline収率 92.8%

試薬・触媒・溶媒 3

HCID 5963Benzyltrimethylammonium chloride触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

2-Ethyl-2-(1H-imidazo[4,5-c]quinolin-1-yl)-1-ethanol (3.0 g, 12.43 mmol), dichloromethane (40 mL), aqueous sodium hydroxide (40 mL of 50%), benzyltrimethylammonium chloride (0.01 g) and 3-chlorobenzyl bromide (2.81 g, 13.67 mmol) were combined and the resulting solution was stirred at ambient temperature overnight. Analysis by TLC (5% methanol in dichloromethane) indicated that the reaction was complete. The reaction was diluted with dichloromethane (100 mL) and water (100 mL). The layers were separated. The aqueous fraction was extracted with dichloromethane. The organic fractions were combined, washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel eluting with ethyl acetate) to provide 4.22 g of 1-(1-{[(3-chlorobenzyl)oxy]methyl}propyl)-1H-imidazo[4,5-c]quinoline as a light orange oil.

後処理

  1. customThe layers were separated
  2. extractionThe aqueous fraction was extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel eluting with ethyl acetate)

出典と根拠

ORDレコード
ord-b7a1204c991f4dd5b4c3f7aace30900a
出典データセット
uspto-grants-2003_12
特許番号
US06670372B2

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