Triethylamine → N-(6,7-Methylenedioxyquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-bromo-3-nitrobenzamide

HRID 1611578

Reaktionsgleichung

Reaktionsgleichung von HRID 1611578
[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[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][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][CH:35]=[C:36]([N+:37]([O-:39])=[O:38])[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 2229532-Bromo-3-nitrobenzoyl chlorideHCID 10923240N'-(6,7-Methylenedioxyquinolin-4-yl)-N,N-dimethylethane-1,2-diamine

Produkt 1

HCID 11070967N-(6,7-Methylenedioxyquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-bromo-3-nitrobenzamideAusbeute 73,9 %

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-3-nitrobenzoic acid chloride in 20 mL of CH2Cl2 (which was prepared by refluxing of 295 mg, 1.2 mmol of 2-bromo-3-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 then washed with saturated NaHCO3 solution, water and brine and dried over Na2SO4. Solvent was removed in vacuo to give 360 mg of a yellow solid (73.9%); mp 96–97° C.; 1H NMR (CDCl3) δ 2.30 (s, 6H), 2.62 (t, 2H, J=6.6), 3.59–3.69 (m, 1H), 4.53–4.67 (m, 1H), 6.18 (d, 2H, J=5.2), 7.05 (d, 1H, J=7.8), 7.14 (d, 1H, J=7.4) 7.28–7.36 (m, 3H) 7.50 (dd, 1H, J=1.2, 7.8), 8.55 (d, 1H, J=3.8); 13C NMR (CDCl3) δ 45.4, 46.5, 56.4, 97.8, 102.3, 106.7, 112.2, 119.5, 122.6, 125.2, 127.7, 129.7, 140.8, 144.6, 148.3, 148.5, 149.5, 151.4, 166.9

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. temperatureto cool
  4. washwashed with saturated NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. customSolvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8f822f3129f6438c9c12c7882ed6bb60
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06989387B2

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