Triethylamine → N-(6,7-Methylenedioxyquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-bromo-4-nitrobenzamide

HRID 1611576

Reaktionsgleichung

Reaktionsgleichung von HRID 1611576
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([NH:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1.C(N(CC)CC)C.[Br:27][C:28]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>C(Cl)Cl>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([N:14]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:30](=[O:31])[C:29]4[CH:33]=[CH:34][C:35]([N+:37]([O-:39])=[O:38])=[CH:36][C:28]=4[Br:27])=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10923240N'-(6,7-Methylenedioxyquinolin-4-yl)-N,N-dimethylethane-1,2-diamineHCID 541029032-Bromo-4-nitrobenzoyl chloride

Produkt 1

HCID 11730633N-(6,7-Methylenedioxyquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-bromo-4-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of compound 7 (259 mg, 1.0 mmol) and triethylamine (0.5 mL) in dry CH2Cl2 (20 mL) was added a solution of 2-bromo-4-nitrobenzoic acid chloride in 20 mL of CH2Cl2 (which was prepared by refluxing of 295 mg, 1.2 mmol of 2-bromo-4-nitrobenzoic acid in 10 mL of thionyl chloride for 4 h). The reaction mixture was heated to reflux for 6 h. The reaction mixture was allowed to cool and was then washed with saturated NaHCO3 solution, water and brine and dried over anhydrous Na2SO4. The solvent was then removed in vacuo to give a yellow solid; yield 345 mg (70.8%); mp 111–112° C.; 1H NMR (CDCl3) δ (2.29, S, 6H), 2.60 (t, 2H, J=6.2), 3.62–3.72 (m, 1H), 4.49–4.62 (m, 1H), 6.19 (d, 2H, J=5.6), 7.12 (d, 1H, J=8.2), 7.37 (s, 3H), 7.75 (d, 1H, J=8) 8.26 (s, 1H), 8.5 (d, 1H, J=4.6); 13C NMR(CDCl3) δ 45.4, 46.6, 56.4, 97.8, 102.4, 106.7, 119.5, 120.6, 121.7, 122.7, 127.6, 128.1, 143.6, 144.4, 147.9, 148.2, 148.5, 149.5, 151.4, 166.8.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. temperatureto cool
  4. washwas then washed with saturated NaHCO3 solution, water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was then removed in vacuo
  7. customto give a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-56220e56c78c452799272b18963dd5ab
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06989387B2

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