2-Methyl-4-methoxyaniline → Ethanol, 2-[[2,3-dihydro-1-(4-methoxy-2-methylphenyl)-6-(trifluoromethoxy)-1H-pyrrolo[3,2-c]quinolin-4-yl]amino]-

HRID 849193ノート

反応式

HRID 849193 の反応式
O=[C:2]1[C:11]2[CH2:12][CH2:13]O[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([O:15][C:16]([F:19])([F:18])[F:17])[C:4]=2[NH:3]1.[CH3:20][C:21]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:22]=1[NH2:23]>C(O)COCCO.[Cl-].[Na+].O>[CH3:20][C:21]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:22]=1[N:23]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([O:15][C:16]([F:19])([F:18])[F:17])[C:4]=3[N:3]=[C:2]([NH:3][CH2:4][CH2:5][OH:15])[C:11]=2[CH2:12][CH2:13]1

参加物

5

反応物 2

HCID 76102-Methyl-4-methoxyanilineHCID 10858582HCID 10858582、化合物

生成物 1

HCID 10113707Ethanol, 2-[[2,3-dihydro-1-(4-methoxy-2-methylphenyl)-6-(trifluoromethoxy)-1H-pyrrolo[3,2-c]quinolin-4-yl]amino]-収率 160.3%

試薬・触媒・溶媒 2

HCID 8117Diethylene Glycol溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
250 °C

実験手順

4-Oxo-6-trifluoromethoxy-2,3,4,5-tetrahydrofuro[3,2-c]quinoline(5.0 g, 19 mmol) was dissolved in diethylene glycol(30 ml) and 2-methyl-4-methoxyaniline(6.1 ml, 46 mmol) was added. The reaction mixture was refluxed at 250° C. for 15 hours, diluted in brine(20 ml), and the aqueous layer was extracted with dichloromethane(15 ml) for 3 times. The organic layer was washed with water(15 ml) for 3 times, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 6.6 g of desired compound as solid in 91% of yield.

後処理

  1. extractionthe aqueous layer was extracted with dichloromethane(15 ml) for 3 times
  2. washThe organic layer was washed with water(15 ml) for 3 times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with ethyl acetate as eluent by silica gel chromatography

出典と根拠

ORDレコード
ord-a32dc391e7634bd2b01512dcd754c897
出典データセット
uspto-grants-2000_01
特許番号
US06011044

反応ノート

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