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

HRID 1280481

반응식

HRID 1280481 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][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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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) δ9.07 (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).

후처리

  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

출처 및 근거

ORD 기록
ord-f56705bbfd1b445bb01ed95c4f43192e
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451810B1

연결된 노트

불러오는 중…