Benzyloxyamine hydrochloride → 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 2105460ノート

反応式

HRID 2105460 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][C:13](=O)[CH2:14][CH2:15][CH3:16].Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([O:26][N:27]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]=[C:13]1[CH2:14][CH2:15][CH3:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

4

反応物 2

HCID 102312Benzyloxyamine hydrochlorideHCID 57447109HCID 57447109、化合物

生成物 1

HCID 675064061-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline収率 29.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of N-(4-chloroquinolin-3-yl)butyramide (3.3 g, 13 mmol, 1.0 eq) and O-benzylhydroxylamine hydrochloride (4.23 g, 26.5 mmol, 2.0 eq) in ethanol (150 mL) was heated at reflux for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane) to provide 1.20 g of 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline.

後処理

  1. temperatureat reflux for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-4764ffd81499413cb32566c89cd248a3
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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