Dimethylformamide → HCID 68154167, 화합물

HRID 341100

반응식

HRID 341100 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N+:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](Cl)=[C:11]([C:20]([O:22]CC)=O)[CH:10]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[NH:39][NH2:40].CN(C)C=O>O.COCCOC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3=[N:40][N:39]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[CH3:32])[C:20](=[O:22])[C:11]3=[CH:10]2)=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 68153930HCID 68153930, 화합물

생성물 1

HCID 68154167HCID 68154167, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

1-[(5-Bromopyridin-2-yl)methyl]-4-chloro-3-(ethoxycarbonyl)quinolinium salt (1.55 g, 3.51 mmol), potassium carbonate (2.63 g, 19.1 mmol, 5.4 equiv), and (2-methylphenyl)hydrazine hydrochloride (1.33 g, 8.38 mmol, 2.4 equiv) were combined in a mixture (1:1) of N,N-dimethylformamide:1,2-dimethoxyethane (25 mL) and placed into an oil bath preheated at 80° C. for 3 hours. The mixture was cooled to ambient temperature, poured into water (100 mL) and extracted with dichloromethane (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol), providing the titled compound as a yellow solid: 1H-NMR (400 MHz, CD3OD) δ 8.97 (1H, s), 8.59 (1H, s), 8.33 (1H, d, J=7.8 Hz), 8.02-8.00 (1H, m), 7.78 (1H, d, J=9.0 Hz), 7.66-7.56 (2H, m), 7.48-7.37 (5H, m), 5.85 (2H, s), 2.28 (3H, s), ppm; low resolution mass spectrometry (ES+) m/z 446.8 [(M+H)+; calculated for C23H17BrN4O: 446.3].

후처리

  1. extractionextracted with dichloromethane (2×100 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol)

출처 및 근거

ORD 기록
ord-873757eabe91491aab7c8f0885940f3c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895580B2

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