2-Oxoglutaric Acid → (6,6-Dimethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij] quinolin-1-yl)Acetic Acid

HRID 983935

반응식

HRID 983935 반응식
Cl.[CH3:2][C:3]1([CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6](N)[CH2:5][CH2:4]1.O=[C:16]([CH2:20][CH2:21]C(O)=O)[C:17]([OH:19])=[O:18]>C(O)(=O)C>[CH3:2][C:3]1([CH3:14])[C:12]2[C:7]3=[C:8]([C:20]([CH2:16][C:17]([OH:19])=[O:18])=[CH:21][N:6]3[CH2:5][CH2:4]1)[CH:9]=[CH:10][CH:11]=2

참가 물질

5

반응물 3

HCID 512-Oxoglutaric AcidHCID 313Hydrochloric AcidHCID 225568373,4-dihydro-4,4-dimethyl-1-(2H)-quinolinamine

생성물 1

HCID 22556735(6,6-Dimethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij] quinolin-1-yl)Acetic Acid수율 34%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of glacial acetic acid (80 mL) and concentrated hydrochloric acid (9 mL) was added 3,4-dihydro-4,4-dimethyl-1-(2H)-quinolinamine (9.5 g, 53.9 mmol) and 2-ketoglutaric acid (9.7 g, 65.1 mmol) and the suspension heated at reflux for 3 hours. After cooling the solvents were removed under reduced pressure and the residue dissolved in 500 mL of ethyl acetate. The ethyl acetate solution was washed with water (3×150 mL) and saturated aqueous sodium chloride (1×50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 1-4% methanol in dichloromethane. Fractions containing product were combined and concentrated under reduced pressure to provide 4.45 g (34%) of the desired compound as a tan foam. An impure fraction was extracted with 1N sodium hydroxice (2×50 mL) and the combined aqueous layers washed with diethyl ether (20 mL) and made acidic with concentrated hydrochloric acid (8 mL). This aqueous mixture was extracted with dichloromethane (2×100 mL), followed by drying (Na2SO4) to provide an additional 2.55 g (19%) of desired product

후처리

  1. temperaturethe suspension heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling the solvents
  4. customwere removed under reduced pressure
  5. dissolutionthe residue dissolved in 500 mL of ethyl acetate
  6. washThe ethyl acetate solution was washed with water (3×150 mL) and saturated aqueous sodium chloride (1×50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washeluting with 1-4% methanol in dichloromethane
  11. additionFractions containing product
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8ae19a585d4c469e8bc974bb30a85519
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867198B2

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