Diethyl Malonate → Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate

HRID 3147

반응식

HRID 3147 반응식
[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O)([CH3:3])[CH3:2].[C:13](OCC)(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[CH:1]([N:4]1[C:5]2[C:6](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]1=[O:20])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 7761Diethyl MalonateHCID 516892Sodium BicarbonateHCID 110410352-((Propan-2-yl)amino)benzaldehyde

생성물 1

HCID 15468682Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate수율 61.3%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

반응 조건

온도
100 °C

실험 절차

A solution of 7.5 g of 2-isopropylaminobenzaldehyde, 11.0 g of diethyl malonate and 11.6 g of sodium bicarbonate in 800 ml of acetic anhydride was stirred under heating at 100° C. for 15 hours. After evaporation of the solvent under reduced pressure, water was added, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 7.3 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate.

후처리

  1. customAfter evaporation of the solvent under reduced pressure, water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-6ea71cac5fe24314936a22d13c05f389
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733917

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