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

HRID 394211ノート

反応式

HRID 394211 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-aa8ce7a44c98442297a7d7da7dc255cf
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

反応ノート

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