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

HRID 1280485

反応式

HRID 1280485 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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) δ9.07 (broad s, 1H), 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).

後処理

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

出典と根拠

ORDレコード
ord-cabfc32635a84629a2fa6017389b0068
出典データセット
uspto-grants-2002_09
特許番号
US06451810B1

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