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

HRID 1611576

반응식

HRID 1611576 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-56220e56c78c452799272b18963dd5ab
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06989387B2

연결된 노트

불러오는 중…