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

HRID 81886

반응식

HRID 81886 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-444e9c8800734027a4b7e3c8451d8e29
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846710B2

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