Hydrochloric Acid → 8-Methoxy-1-ethyl-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

HRID 503984ノート

反応式

HRID 503984 の反応式
[CH3:1][O:2][C:3]1[C:12]2[NH:11][C:10](=[O:13])[CH2:9][CH2:8][C:7]=2[C:6]([CH:14]=[O:15])=[CH:5][CH:4]=1.[H-].[Na+].[H][H].[CH2:20](I)[CH3:21].Cl>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]2[N:11]([CH2:20][CH3:21])[C:10](=[O:13])[CH2:9][CH2:8][C:7]=2[C:6]([CH:14]=[O:15])=[CH:5][CH:4]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 859802658-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehydeHCID 178418361HCID 178418361、化合物

生成物 1

HCID 866139138-Methoxy-1-ethyl-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde収率 91%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

8-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde (2.0 g) was dissolved in DMF (20 ml), and 0.43 g of sodium hydride (60% in oil) was added under ice cooling. After the addition, stirring was carried out at room temperature until the generation of hydrogen stopped. The resulting mixture was cooled in an ice water bath again, 1.2 ml of ethyl iodide was added dropwise, and stirring was carried out at room temperature for 8 hours. The reaction mixture was poured into iced aqueous hydrochloric acid, extraction with methylene chloride was performed, and the organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to thereby obtain 2.1 g (yield: 91%) of 8-methoxy-1-ethyl-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde.

後処理

  1. additionAfter the addition
  2. temperatureThe resulting mixture was cooled in an ice water bath again
  3. stirringstirring
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4ae294169ba7466982348fd3a64944ff
出典データセット
uspto-grants-2010_08
特許番号
US07777038B2

反応ノート

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