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

HRID 503984노트

반응식

HRID 503984 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4ae294169ba7466982348fd3a64944ff
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07777038B2

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