Methyl Methacrylate → 10-bromo-2-methoxy-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-one

HRID 850753ノート

反応式

HRID 850753 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=3.[C:17](OC)(=[O:21])[C:18]([CH3:20])=[CH2:19]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[C:18]([CH3:20])[C:17](=[O:21])[C:8]4[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

参加物

4

反応物 2

HCID 6658Methyl MethacrylateHCID 15886922HCID 15886922、化合物

生成物 1

HCID 2125282210-bromo-2-methoxy-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-one収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-bromo-6-methoxycarbazole (20 g) produced in Example 1, step 1 was dissolved in anhydrous tetrahydrofuran (200 ml), and to the solution were added methyl methacrylate (77.6 ml), then Triton B (0.7 ml). The mixture was heated under reflux in an argon atmosphere for 2 hours, and the solvent was evaporated under reduced pressure. The resulting residue was suspended in methanol (60 ml), and sodium hydroxide (6.4 g) dissolved in water (80 ml) was added dropwise at room temperature, and the mixture was stirred at room temperature for 12 hours. The solvent was evaporated under reduced pressure, and water and ether were added for phase separation. The aqueous layer was rendered acidic by addition of 4N hydrochloric acid, and ethyl acetate was added for further phase separation. The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residual crude crystals were washed with hexane and ether and recovered by filtration to obtain the title compound (25.0 g, 95%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux in an argon atmosphere for 2 hours
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionsodium hydroxide (6.4 g) dissolved in water (80 ml)
  5. additionwas added dropwise at room temperature
  6. customThe solvent was evaporated under reduced pressure, and water and ether
  7. additionwere added for phase separation
  8. additionThe aqueous layer was rendered acidic by addition of 4N hydrochloric acid, and ethyl acetate
  9. additionwas added for further phase separation
  10. washThe ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous sodium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. washThe residual crude crystals were washed with hexane and ether
  14. filtrationrecovered by filtration

出典と根拠

ORDレコード
ord-e039dae022f94c45b83846407354480c
出典データセット
uspto-grants-2000_01
特許番号
US06018046

反応ノート

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