Sodium Acetate → Ethyl 5-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 73891노트

반응식

HRID 73891 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10](Br)[CH:11]=[CH:12][C:13]=2[O:17][CH3:18])[NH:8][CH:7]=1)=[O:5])[CH3:2].C([O-])(=O)C.[Na+]>C(O)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:17][CH3:18])[NH:8][CH:7]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 517045Sodium AcetateHCID 102458028-bromo-4-hydroxy-5-methoxy-3-Quinolinecarboxylic acid ethyl ester

생성물 1

HCID 9992162Ethyl 5-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate수율 57%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

A mixture of 8-bromo-5-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (2.3 g, 7.1 mmol), sodium acetate (580 mg, 7.1 mmol) and 10% Pd/C (100 mg) in glacial acetic acid (50 ml) was stirred under H2 (2.5 atm) overnight. The catalyst was removed via filtration, and the reaction mixture was concentrated under reduced pressure. The resulting oil was dissolved in CH2Cl2 (100 mL) and washed with aqueous sodium bicarbonate solution and water. The organic layer was dried, filtered and concentrated. The crude product was purified by column chromatography to afford 5-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester as a yellow solid (1 g, 57%).

후처리

  1. customThe catalyst was removed via filtration
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe resulting oil was dissolved in CH2Cl2 (100 mL)
  4. washwashed with aqueous sodium bicarbonate solution and water
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-03e27bbdc6764e1aa4d5e85400fabd70
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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