Ethyl Acetate → Ethyl 1-bromo-4-oxo-4H-quinolizine-3-carboxylate

HRID 48907노트

반응식

HRID 48907 반응식
[O:1]=[C:2]1[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10]2)=[CH:5][CH:4]=[C:3]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[Br:17]Br.C(OCC)(=O)C>C(O)(=O)C>[Br:17][C:5]1[CH:4]=[C:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2](=[O:1])[N:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[CH:10]2

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 4615166Ethyl 4-oxo-4H-quinolizine-3-carboxylate

생성물 1

HCID 20634149Ethyl 1-bromo-4-oxo-4H-quinolizine-3-carboxylate수율 71%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

To a solution of ethyl 4-oxo-4H-quinolizine-3-carboxylate (1) (2.33 g, 10.7 mmol) in 20 ml acetic acid was rapidly added a solution of bromine (1.9 g, 12 mmol) in 10 ml acetic acid. The reaction was complete after 5 min, as indicated by thin layer chromatography (ethyl acetate). The solvent was evaporated in vacuo and the remaining yellow solid was dissolved in 20 ml dichloromethane. To this solution, silica gel (3 g) was added and the solvent was evaporated in vacuo. The silica gel was poured on a prepacked column and eluted with ethyl acetate to give ethyl 1-bromo-4-oxo-4H-quinolizine-3-carboxylate (9) as a bright yellow solid (2.1 g, 71%). M.p. 156-158° C. 1H NMR (δ, CDCl3): 1.43 (t, J=7 Hz, 3H), 4.43 (q, J=7 Hz, 2H), 7.03 (dd, J=7 Hz, J=7 Hz, 1H), 7.30 (dd, J=7 Hz, 2H), 7.80 (dd, J=7 Hz, J=7 Hz, 1H), 8.63 (s, 1H), 9.49 (d, J=7 Hz). MS: m/z 294.9839; required for C12H10BrNO3: 294.9843.

후처리

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe remaining yellow solid was dissolved in 20 ml dichloromethane
  3. additionTo this solution, silica gel (3 g) was added
  4. customthe solvent was evaporated in vacuo
  5. additionThe silica gel was poured on a prepacked column
  6. washeluted with ethyl acetate

출처 및 근거

ORD 기록
ord-d3178d8e91d04267aa1ceb80d6bc1c57
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706528B2

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