Triethylamine → N-{5-[(3-nitroquinolin-4-yl)amino]pentyl}benzamide

HRID 746503

反応式

HRID 746503 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][CH2:27][CH2:28][NH:29][C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)(Cl)Cl>[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][CH2:27][CH2:28][NH:29][C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)([O-:22])=[O:21]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 345353N-(5-Aminopentyl)benzamideHCID 224789924-Chloro-3-nitroquinoline hydrochloride

生成物 1

HCID 23512735N-{5-[(3-nitroquinolin-4-yl)amino]pentyl}benzamide収率 84.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

Triethylamine (1 eq.) was added to a suspension of 4-chloro-3-nitroquinoline hydrochloride (13 g, 53 mmol) in chloroform. A suspension of N-(5-aminopentyl)benzamide (11 g, 53 mmol) in chloroform was added and the reaction mixture was heated to reflux. Progress of the reaction was monitored by HPLC. The reaction mixture was concentrated under vacuum. The residue was diluted with toluene, heated to reflux and then filtered while still hot. The filtrate was allowed to cool. The resulting precipitate was isolated by filtration to provide 16.9 g of N1-{5-[(3-nitroquinolin-4-yl)amino]pentyl}benzamide as a yellow solid, m.p. 130-132-C. 1H NMR (500 MHz, DMSO-d6) δ 9.07 (s, 1H), 9.02 (broad s, 1H), 8.53 (d, J=8.0 Hz, 1H), 8.43 (t, J=6.0 Hz, 1H), 7.89 (dd, J=8.0, 1.2 Hz, 1H), 7.83 (dt, J=8.0, 1.2 Hz, 1H), 7.80 (d, J=8.0 Hz, 2H), 7.57 (dt, J=8.0, 1.2 Hz, 1H), 7.50 (t, J=8.0 Hz, 1H), 7.43 (t, J=8.0 Hz, 2H), 3.63 (q, J=6.0 Hz, 2H), 3.25 (q, J=6.0 Hz, 2H), 1.77 (quintet, J=7.0 Hz, 2H), 1.55 (quintet, J=7.0 Hz, 2H), 1.39 (quintet, J=7.0 Hz, 2H).

後処理

  1. additionwas added
  2. temperaturethe reaction mixture was heated to reflux
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionThe residue was diluted with toluene
  5. temperatureheated
  6. temperatureto reflux
  7. filtrationfiltered while still hot
  8. temperatureto cool
  9. customThe resulting precipitate was isolated by filtration

出典と根拠

ORDレコード
ord-0713891229dc46239fb03e69a8116ae1
出典データセット
uspto-grants-2008_07
特許番号
US07393859B2

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