Butyryl chloride → 7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 9465

反応式

HRID 9465 の反応式
[C:1](Cl)(=O)[CH2:2][CH2:3][CH3:4].[Br:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([NH:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[C:13]([NH2:18])[CH:14]=[N:15]2)=[CH:10][CH:9]=1>N1C=CC=CC=1.[Au]>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:1]([CH2:2][CH2:3][CH3:4])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1

参加物

5

反応物 2

HCID 8855Butyryl chlorideHCID 688181597-bromo-N4-isobutylquinoline-3,4-diamine

生成物 1

HCID 219842557-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinoline

試薬・触媒・溶媒 2

HCID 23985Gold触媒HCID 1049Pyridine溶媒

実験手順

Butyryl chloride (1.1 equivalent) was slowly added to a stirred solution of 7-bromo-N4-(2-methylpropyl)quinoline-3,4-diamine (52.9 g, 0.18 mol.) in pyridine (700 mL) at room temperature. A pale yellow precipitate formed and then went into solution. The reaction mixture was heated at reflux for eight hours, and then allowed to slowly cool to room temperature over the weekend. The dark gold, turbid reaction mixture was concentrated under reduced pressure. The residue was dissolved in 1 N hydrochloric acid and then adjusted to pH 14 with the addition of 10% aqueous sodium hydroxide. A precipitate formed, was isolated by filtration, washed with water (3×100 mL), and dried overnight on the filter funnel to provide 7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinoline as an off-white solid.

後処理

  1. customA pale yellow precipitate formed
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for eight hours
  4. concentrationwas concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 1 N hydrochloric acid
  6. additionadjusted to pH 14 with the addition of 10% aqueous sodium hydroxide
  7. customA precipitate formed
  8. customwas isolated by filtration
  9. washwashed with water (3×100 mL)
  10. customdried overnight on the filter funnel

出典と根拠

ORDレコード
ord-e8cfcc7d7bdb4706b163b70ba212038d
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

関連ノート

読み込み中…