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4-(Benzyloxy)-2-methylaniline → 1-(2-Methyl-4-benzyloxyphenyl)-4-[(2-hydroxyethyl)amino]-6-beta,beta,beta-trifluoroethoxy-2,3-dihydropyrrolo[3,2-c]quinoline

HRID 849216
ノート
印刷プレビュー

反応式

HRID 849216 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][CH2:16][C:17]([F:20])([F:19])[F:18])[C:4]=2[NH:3]1.[CH2:21]([O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[C:31]([CH3:36])[CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)COCCO.O>[CH3:36][C:31]1[CH:30]=[C:29]([O:28][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:35]=[CH:34][C:32]=1[N:33]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[C:4]=3[N:3]=[C:2]([NH:3][CH2:4][CH2:5][OH:15])[C:11]=2[CH2:12][CH2:13]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 167730534-(Benzyloxy)-2-methylanilineHCID 193698434-Oxo-6-beta,beta,beta-trifluoroethoxy-2,3,4,5-tetrahydrofuro[3,2-c]quinoline

生成物 1

HCID 193698341-(2-Methyl-4-benzyloxyphenyl)-4-[(2-hydroxyethyl)amino]-6-beta,beta,beta-trifluoroethoxy-2,3-dihydropyrrolo[3,2-c]quinoline収率 86%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8117
Diethylene Glycol
溶媒

反応条件

温度
250 °C

実験手順

4-Oxo-6-β,β,β-trifluoroethoxy-2,3,4,5-tetrahydrofuro[3,2-c]quinoline(5.7 g, 20.0 mmol) was dissolved in diethylene glycol(70 ml) and crude 4-benzyloxy-2-methyl aniline(5.6 g, 26.0 mmol) was added. The reaction mixture was refluxed at 250° C. for 15 hours. The reaction mixture was dissolved in water, extracted with dichloromethane, and the organic layer was washed with water for 3 times. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography(ethyl acetate:dichloromethane=1:1) to obtain 4.5 g of desired compound as solid in 47% of yield.

後処理

  1. extractionextracted with dichloromethane
  2. washthe organic layer was washed with water for 3 times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography(ethyl acetate:dichloromethane=1:1)

出典と根拠

ORDレコード
ord-eac70824543a4d88831844bc2ef6e005
出典データセット
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06011044

反応ノート

読み込み中…

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