Potassium Carbonate → 3-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester

HRID 1819770ノート

反応式

HRID 1819770 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([OH:15])=[CH:10]2)=[O:4].[Cl:16][C:17]1[CH:18]=[C:19]([N+:25]([O-:27])=[O:26])[CH:20]=[C:21]([Cl:24])[C:22]=1Cl.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:22]1[C:21]([Cl:24])=[CH:20][C:19]([N+:25]([O-:27])=[O:26])=[CH:18][C:17]=1[Cl:16])=[CH:10]2)=[O:4]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 883653,4,5-TrichloronitrobenzeneHCID 57440941Methyl 3-hydroxyquinoline-8-carboxylate

生成物 1

HCID 574409423-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 3-Hydroxy-8-quinolinecarboxylic acid methyl ester (97) (256 mg, 1.26 mmol) and 3,4,5-trichloronitrobenzene (294 mg, 1.30 mmol) in acetone (40 mL) was added K2CO3 (870 mg, 6.30 mmol). This mixture was refluxed for 3.5 h. The reaction mixture was cooled to room temperature and insoluble materials were removed by Celite filtration. The filtrate was concentrated and the residue was purified by column chromatography. (hexane/AcOEt=4/1, 80 g of silica gel) to afford compound 98. 1H NMR (300 MHz, DMSO-d6) δ 3.92 (3H, s), 7.67 (1H, dd, J=7.3 Hz), 7.79 (1H, d, J=2.9 Hz), 7.88 (1H, dd, J=1.5, 7.3 Hz), 9.05 (1H, d, J=2.9 Hz).

後処理

  1. temperatureThis mixture was refluxed for 3.5 h
  2. custominsoluble materials were removed by Celite filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-b27e6c942dec411d8819b6390271a6d8
出典データセット
uspto-grants-2009_10
特許番号
US07601841B2

反応ノート

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