Triethylamine → N1-(3-nitroquinolin-1-yl)-2-methylpropane-1,2-diamine

HRID 1925461

反応式

HRID 1925461 の反応式
[NH2:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4].C(N(CC)CC)C.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26]>ClCCl>[N+:25]([C:16]1[CH2:17][N:18]([NH:1][CH2:2][C:3]([CH3:5])([NH2:6])[CH3:4])[C:19]2[C:24]([CH:15]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)([O-:27])=[O:26]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 112758084-Chloro-3-nitroquinoline

生成物 1

HCID 86626603N1-(3-nitroquinolin-1-yl)-2-methylpropane-1,2-diamine収率 99.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Under a nitrogen atmosphere, a solution of 1,2-diamino-2-methylpropane (52.20 mL, 503.3 mmol), triethylamine (131.8 mL, 958.8 mmol), and dichloromethane (1.0 L) was chilled in an ice water bath. 4-Chloro-3-nitroquinoline (100.0 g, 479.4 mmol) was added in portions over a period of 5 minutes. The reaction mixture was stirred at 0° C. for 2 hours and then allowed to slowly warm to ambient temperature. After 16 hours the reaction mixture was concentrated under reduced pressure. The residue was triturated with water (500 mL) for 1 hour. The resulting solid was isolated by filtration and dried overnight in a vacuum desiccator to provide 124.6 g of N1-(3-nitroquinolin-1-yl)-2-methylpropane-1,2-diamine as a yellow crystalline solid.

後処理

  1. temperatureto slowly warm to ambient temperature
  2. concentrationAfter 16 hours the reaction mixture was concentrated under reduced pressure
  3. customThe residue was triturated with water (500 mL) for 1 hour
  4. customThe resulting solid was isolated by filtration
  5. customdried overnight in a vacuum desiccator

出典と根拠

ORDレコード
ord-8a8989253b5349c0afd5f6e981c9a991
出典データセット
uspto-grants-2012_05
特許番号
US08178677B2

関連ノート

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