Triethylamine → N1-{3-[(3-nitroquinolin-4-yl)amino]propyl}benzamide

HRID 746507

반응식

HRID 746507 반응식
C(N(CC)CC)C.Cl.Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21].[NH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl>[N+:20]([C:11]1[CH:12]=[N:13][C:14]2[C:19]([C:10]=1[NH:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)([O-:22])=[O:21]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 238993n-(3-Aminopropyl)benzamideHCID 224789924-Chloro-3-nitroquinoline hydrochloride

생성물 1

HCID 23512704N1-{3-[(3-nitroquinolin-4-yl)amino]propyl}benzamide수율 25.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Triethylamine (9.3 mL, 67 mmol) was added to a mixture of 4-chloro-3-nitroquinoline hydrochloride (16.4 g, 67 mmol) and dichloromethane (400 mL). A solution of N-(3-aminopropyl)benzamide (11.9 g, 67 mmol) in dichloromethane (100 mL) was added all a once. The reaction mixture was stirred at ambient temperature for 1 hour and then heated on a steam bath for 1 hour. The resulting precipitate was isolated by filtration to provide 6 g of N1-{3-[(3-nitroquinolin-4-yl)amino]propyl}benzamide as a yellow solid, m.p. 209-211° C. 1H NMR (500 MHz, DMSO-d6) δ 9.07 (broad s, I—H), 9.05 (s, 1H), 8.54 (t, J=6.0 Hz, 1H), 8.51 (d, J=8.0 Hz, 1H), 7.89 (d, J=8.0 Hz, 1H), 7.82 (t, J=8.0 Hz, 1H), 7.76 (d, J=8.0 Hz, 2H), 7.55 (t, J=8.0 Hz, 1H), 7.50 (t, J=8.0 Hz, 1H), 7.43 (t, J=8.0 Hz, 2H), 3.69 (q, J=6.0 Hz, 2H), 3.35 (q, J=6.0 Hz, 2H), 2.00 (quintet, J=7.0 Hz, 2H).

후처리

  1. temperatureheated on a steam bath for 1 hour
  2. customThe resulting precipitate was isolated by filtration

출처 및 근거

ORD 기록
ord-6ed452fb6262454aa052283ad5a0e8d4
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393859B2

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