Aniline → 1-(Phenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

HRID 1416670ノート

反応式

HRID 1416670 の反応式
[O:1]=[C:2]1[CH:11]2[CH2:12][CH2:13]O[C:10]2=[C:9]2[C:4]([C:5]([O:15][CH3:16])=[CH:6][CH:7]=[CH:8]2)=[N:3]1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(O)C=CC=CC=1.O>[C:18]1([N:17]2[C:10]3[C:9]4[CH:8]=[CH:7][CH:6]=[C:5]([O:15][CH3:16])[C:4]=4[NH:3][C:2](=[O:1])[C:11]=3[CH2:12][CH2:13]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 2

HCID 6115AnilineHCID 676260994-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline

生成物 1

HCID 158088531-(Phenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline収率 82.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 996Phenol溶媒

反応条件

温度
190 °C

実験手順

4-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline (217 mg, 1.0 mmol) was dissolved in 7 ml of phenol and aniline (228 μl, 2.5 mmol) was added under nitrogen. The reaction mixture was heated at 190° C. for 15 hours. The reaction mixture was diluted with 20 ml of salt water and the aqueous layer was extracted with methylene chloride (15 ml×3). After washing with water (15 ml×3), the organic layer was dried by anhydrous magnesium surface and filtered, and concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 240 mg of desired compound as solid in 83% of yield.

後処理

  1. extractionthe aqueous layer was extracted with methylene chloride (15 ml×3)
  2. washAfter washing with water (15 ml×3)
  3. customthe organic layer was dried by anhydrous magnesium surface
  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-36e47219e5a74fd0ba239f883256b0d5
出典データセット
uspto-grants-1999_06
特許番号
US05914402

反応ノート

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