Sodium Hydroxide → 2-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

HRID 1637257ノート

反応式

HRID 1637257 の反応式
[C:1]1([CH:7]2[CH:15]3[CH2:16][CH2:17][C:18](=[O:19])[C:13]4[C:14]3=[C:9]([CH:10]=[CH:11][CH:12]=4)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl.[OH-].[Na+]>O1CCCC1>[C:1]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:18](=[O:19])[CH2:17][CH2:16][C:15]=2[C:14]=34)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 73252o-ChloranilHCID 193482872-Phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

生成物 1

HCID 193483682-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one収率 70.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A portion (3.3 g) of the compound obtained in Example 22 was dissolved in anhydrous tetrahydrofuran (THF; 400 ml) and to the solution was added o-chloranil (3.6 g). The resulting mixture was stirred for 30 minutes at room temperature. After adding 1N aqueous solution of sodium hydroxide, the reaction mixture was extracted twice with ethyl acetate. The organic layers were combined, washed twice with 1N aqueous solution of sodium hydroxide and once with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (methylene chloride) and further crystallized from an ether/hexane mixed solvent to yield 2.3 g (70%) of the titled compound as crystals.

後処理

  1. extractionthe reaction mixture was extracted twice with ethyl acetate
  2. washwashed twice with 1N aqueous solution of sodium hydroxide and once with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (methylene chloride)
  6. customfurther crystallized from an ether/hexane mixed solvent

出典と根拠

ORDレコード
ord-132352bb25074d3bb14ad1e95960d078
出典データセット
uspto-grants-2000_03
特許番号
US06040331

反応ノート

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