Water → Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

HRID 394211노트

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HRID 394211 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18](N)=[O:19])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:29])[N:13]2[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28].[OH-].[Na+].O.Cl[O-].[Na+].[O:36]1CCOC[CH2:37]1>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]([O:36][CH3:37])=[O:19])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:29])[N:13]2[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28]

참가 물질

7

반응물 5

HCID 962WaterHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 226479965-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxamideHCID 23665760Sodium Hypochlorite

생성물 1

HCID 22648161Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

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온도
60 °C

실험 절차

To 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxamide (920 mg) in dioxane (330 mL) was added 5N NaOH (10 mL) and water (41 mL) followed by sodium hypochlorite (19.3 mL of a 10-13% aqueous solution) and the reaction mixture heated to 60° C. for 2 h. The cooled reaction mixture was then poured into brine and extracted into ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.61-7.32 (m, 8H); 6.48 (d, J=2.1 Hz, 1H); 6.45 (d, J=9.7 Hz, 1H); 5.73 (d, J=2.1 Hz, 1H; 4.00 (br.s, 2H). Mass spectrum: m/z 415 (M+H).

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted into ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-aa8ce7a44c98442297a7d7da7dc255cf
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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