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Triethylamine → HCID 178492080, 화합물

HRID 1600029
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HRID 1600029 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:20])=[C:7]([C:16]([O:18]C)=O)[C:8]([C:12]([O:14]C)=O)=[N:9]2)=[CH:4][CH:3]=1.Cl.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][NH2:31])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:20])[C:7]3[C:16]([OH:18])=[N:31][N:30]([C:27]4[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=4)[C:12](=[O:14])[C:8]=3[NH:9][C:10]=2[CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 178418477HCID 178418477, 화합물

생성물 1

HCID 178492080HCID 178492080, 화합물수율 112%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred suspension of dimethyl 7-chloro-4-hydroxyquinoline-2,3-dicarboxylate (0.500 g, 1.69 mM) in ethanol (17mL) was added 4-methoxyphenyl hydrazine hydrochloride (2.07 g, 11.83 mM). Triethylamine (1.88 mL, 13.52 mM) was added, and the mixture was heated to reflux for 40 hours. The resulting suspension was filtered hot, and the collected solids were washed with ethanol to give the 4-methoxyphenyl hydrazine salt of the title compound (0.700 g) as a light tan solid. This material was heated to reflux in glacial acetic acid (20 mL) for 2 hours to give a brown suspension. The suspension was cooled to room temperature. The solids were collected and washed with glacial aceticacid, methanol and ether to give the title compound (0.331 g, 53%) as a tanpowder, mp 365° C. (decomp.); MS(CI): 370 (M+H). Analysis for C18H12ClN3O4 : Calculated: C, 58.50; H, 3.27; N, 11.36; Found: C, 58.29; H, 3.41; N, 11.14; NMR: 13.79 (br s, 1H, exchangeable), 8.22 (br d, J=8.70 Hz, 2H, 1H exchangeable), 7.88 (d, J=1.79 Hz, 1H), 7.57 (dd, J=1.79, 8.70 Hz, 1H), 6.78 (s, 4H), 3.67 (s, 3H).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 40 hours
  3. filtrationThe resulting suspension was filtered hot
  4. washthe collected solids were washed with ethanol

출처 및 근거

ORD 기록
ord-d6009f902559468189ac995931e9398c
출처 데이터셋
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05744471

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