Dimethylformamide → Ethyl 8-Azido-4-Oxo-4H-Quinolizine-3-Carboxylate

HRID 48910

반응식

HRID 48910 반응식
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2=[O:17].[N-:18]=[N+:19]=[N-:20].[Na+].CN(C=O)C>O>[N:18]([C:2]1[CH:3]=[CH:4][N:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2=[O:17])=[N+:19]=[N-:20]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 3314858Ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate

생성물 1

HCID 20634157Ethyl 8-Azido-4-Oxo-4H-Quinolizine-3-Carboxylate수율 85%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

An oven-dried 25 ml round-bottom flask was purged with argon and charged with ethyl 8-chloro-4-oxo-4H-quinolizine-3-carboxylate (2) (250 mg, 1 mmol), NaN3 (300 mg, 4.6 mmol), and 5 ml DMF. The reaction mixture was stirred at 40° C. for 1 h, cooled to room temperature, and poured into 100 ml water. The aqueous layer was extracted three times with 100 ml chloroform, and the combined organic layers were washed three times with 100 ml water. The organic solvent was evaporated and the crude product was purified by flash chromatography (ethyl acetate) to give a deep red crystalline solid (218 mg, 85%). M.p. 145-150° C. 1H NMR (δ, CDCl3): 1.42 (t, J=7 Hz, 3H), 4.41 (q, J=7 Hz, 2H), 6.53 (d, J=8 Hz, 1H), 6.84 (dd, J=2 Hz, J=7 Hz, 1H), 7.08 (d, J=2 Hz, 1H), 8.37 (d, J=8 Hz, 1H), 9.36 (d, J=7 Hz, 1H). MS: m/z 258.0751; required for C12H10N4O3: 258.0753.

후처리

  1. customAn oven-dried 25 ml round-bottom flask was purged with argon
  2. temperaturecooled to room temperature
  3. extractionThe aqueous layer was extracted three times with 100 ml chloroform
  4. washthe combined organic layers were washed three times with 100 ml water
  5. customThe organic solvent was evaporated
  6. customthe crude product was purified by flash chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-00124a126b114070a4139697ee5b43e7
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706528B2

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