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

HRID 3147

反応式

HRID 3147 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6ea71cac5fe24314936a22d13c05f389
出典データセット
uspto-grants-1998_03
特許番号
US05733917

関連ノート

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