Dimethylformamide → Ethyl 8-(3-Nitrophenoxy)-4-Oxo-4H-Quinolizine-3-Carboxylate

HRID 48912

반응식

HRID 48912 반응식
[H-].[Na+].CN(C=O)C.[N+:8]([C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].Cl[C:19]1[CH:20]=[CH:21][N:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:23]2=[O:34]>O.C(OCC)(=O)C>[N+:8]([C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][C:19]1[CH:20]=[CH:21][N:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:23]2=[O:34])([O-:10])=[O:9]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 111373-NitrophenolHCID 24758Sodium hydrideHCID 3314858Ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate

생성물 1

HCID 20634154Ethyl 8-(3-Nitrophenoxy)-4-Oxo-4H-Quinolizine-3-Carboxylate수율 67%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

An oven-dried 50 ml three-necked round-bottom flask was purged with argon and charged with sodium hydride (200 mg, 60% suspension in oil, 5 mmol and washed with hexane) and 10 ml dry DMF. To this suspension, m-nitrophenol (626 mg, 4.5 mmol) was added in one portion. After gas evolution had ceased, ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate (2) (1.00 g, 4 mmol) was added in one portion and stirring was continued at room temperature for 2 h. When the reaction was complete as indicated by thin layer chromatography (ethyl acetate), the reaction mixture was poured into 250 ml of water. The aqueous layer was extracted three times with 200 ml dichloromethane, and the combined organic layers were washed three times with 200 ml water. The organic solvent was evaporated and the crude product was stirred overnight with 30 ml ether. Filtration gave a bright yellow solid (950 mg, 67%). M.p. 161-163° C. 1H NMR (δ, CDCl3): 1.42 (t, J=7 Hz, 3H), 4.41 (q, J=7 Hz, 2H), 6.39 (d, J=8 Hz, 1H), 6.70 (d, J=2 Hz, 1H), 6.99 (dd, J=0.5 Hz, J=7 Hz, 1H), 7.55 (d, J=7 Hz, 1H), 7.72 (dd, J=8 Hz, J=8 Hz, 1H), 8.07 (s, 1H), 8.24 (d, J=8 Hz, 1H), 8.32 (d, J=8 Hz, 1H), 9.43 (d, J=7 Hz, 1H). MS: m/z 354.0850; required for C18H14N2O6: 354.0852.

후처리

  1. customAn oven-dried 50 ml three-necked round-bottom flask was purged with argon
  2. extractionThe aqueous layer was extracted three times with 200 ml dichloromethane
  3. washthe combined organic layers were washed three times with 200 ml water
  4. customThe organic solvent was evaporated
  5. stirringthe crude product was stirred overnight with 30 ml ether
  6. filtrationFiltration

출처 및 근거

ORD 기록
ord-8a29caaef06443a9996ee9bb3f54bec8
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706528B2

연결된 노트

불러오는 중…