Ammonia → 2-Chloro-1,4-dihydro-1,4-dioxo-3-(2-oxopiperidino)naphthalene

HRID 1582184ノート

反応式

HRID 1582184 の反応式
[H-].[Na+].[O:3]=[C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]1.[Cl:10][C:11]1[C:12](=[O:23])[C:13]2[C:18]([C:19](=[O:22])[C:20]=1Cl)=[CH:17][CH:16]=[CH:15][CH:14]=2.N>CN(C=O)C>[Cl:10][C:11]1[C:12](=[O:23])[C:13]2[C:18]([C:19](=[O:22])[C:20]=1[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:4]1=[O:3])=[CH:17][CH:16]=[CH:15][CH:14]=2

参加物

6

反応物 4

HCID 222AmmoniaHCID 8342DichloneHCID 126652-PiperidoneHCID 24758Sodium hydride

生成物 1

HCID 227199642-Chloro-1,4-dihydro-1,4-dioxo-3-(2-oxopiperidino)naphthalene収率 16.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

NaH (440 mg) was added to a solution of 2-oxopiperidine (1.0 g) in DMF (20 ml) and the mixture was stirred at room temperature for 30 minutes. This solution was added in a single portion to a solution of 2,3-dichloro-1,4-dihydro-1,4-dioxonaphthalene (6.9 g) in DMF (150 ml) and the mixture was stirred at room temperature for 17 hours. The reaction solution was poured into saturated aqueous ammonia and the resulting precipitate was removed by filtration and then the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (elution with ethyl acetate-hexane 1:10 solution) to give 2-chloro-1,4-dihydro-1,4-dioxo-3-(2-oxopiperidino)naphthalene (0.49 g) as a light brown powder.

後処理

  1. stirringthe mixture was stirred at room temperature for 17 hours
  2. customthe resulting precipitate was removed by filtration
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (elution with ethyl acetate-hexane 1:10 solution)

出典と根拠

ORDレコード
ord-dc5ce09b17744f199075001d5ba00870
出典データセット
uspto-grants-2004_05
特許番号
US06734203B2

反応ノート

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