Picolinic acid → Diethyl 2-(2-methylquinolin-7-yl)malonate

HRID 339075노트

반응식

HRID 339075 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1C(O)=O.C([O-])([O-])=O.[Cs+].[Cs+].[C:28]([O:36][CH2:37][CH3:38])(=[O:35])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>O1CCOCC1.O.C(OCC)(=O)C>[CH3:12][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:28]([O:36][CH2:37][CH3:38])=[O:35])=[CH:3][CH:4]=2)[N:9]=1

참가 물질

8

반응물 4

HCID 1018Picolinic acidHCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 123328967-Bromo-2-methylquinoline

생성물 1

HCID 70984111Diethyl 2-(2-methylquinolin-7-yl)malonate수율 26%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A mixture of 7-bromo-2-methylquinoline (2.00 g, 9.01 mmol), Cu(I)I (0.172 g, 0.90 mmol), picolinic acid (0.222 g, 1.80 mmol), Cs2CO3 (8.80 g, 27.0 mmol) and diethyl malonate (2.73 mL, 18.0 mmol) in dioxane (25 mL) was stirred at 100° C. for hours. After cooling to ambient temperature, ethyl acetate (30 mL) and water (15 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue obtained was purified by flash chromatography on silica gel (3:2 hexane/ethyl acetate) to give diethyl 2-(2-methylquinolin-7-yl)malonate (0.7 g, 2.32 mmol, 26% yield) as oil.

후처리

  1. temperatureAfter cooling to ambient temperature
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by flash chromatography on silica gel (3:2 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-f254e49f4fea4f2aa859f138dfbcc5e9
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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