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

HRID 746503

Reaction equation

HRID 746503 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0713891229dc46239fb03e69a8116ae1
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Linked notes

Loading…