O-ethylhydroxylamine hydrochloride → 1-ethoxy-1H-imidazo[4,5-c]quinoline

HRID 2105480ノート

反応式

HRID 2105480 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][CH:13]=O.Cl.[CH2:16]([O:18][NH2:19])[CH3:17]>C(O)(C)C>[CH2:16]([O:18][N:19]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[CH:13]1)[CH3:17]

参加物

4

反応物 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 86227468N-(4-chloroquinolin-3-yl)formamide

生成物 1

HCID 675069551-ethoxy-1H-imidazo[4,5-c]quinoline収率 47.9%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A solution of 4-chloroquinolin-3-ylformamide (5.0 g, 24 mmol), O-ethylhydroxylamine hydrochloride (2.95 g, 30.2 mmol), and isopropanol (75 mL) was heated at reflux overnight, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was stirred with dichloromethane (150 mL) and saturated aqueous sodium carbonate (50 mL) for 15 minutes. The organic layer was separated and dried over potassium carbonate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent) to provide 2.45 g of 1-ethoxy-1H-imidazo[4,5-c]quinoline.

後処理

  1. temperatureat reflux overnight
  2. concentrationconcentrated under reduced pressure
  3. customThe organic layer was separated
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (eluting with 2% methanol in dichloromethane containing 5 mL of aqueous ammonium hydroxide per liter of eluent)

出典と根拠

ORDレコード
ord-a91af1a69f174bea8db4f7f02889b41c
出典データセット
uspto-grants-2009_08
特許番号
US07579359B2

反応ノート

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