Allyl bromide → 5,6,7,8-tetrahydro-5-oxo-1-(2-propenyl)-2(1H)-quinolinone

HRID 1586992노트

반응식

HRID 1586992 반응식
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[NH:7][C:6](=[O:12])[CH:5]=[CH:4][C:3]1=2.[H-].[Li+].Br[CH2:16][CH:17]=[CH2:18]>CN(C)C=O>[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]([CH2:18][CH:17]=[CH2:16])[C:6](=[O:12])[CH:5]=[CH:4][C:3]1=2

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 62714Lithium hydrideHCID 2674502-Hydroxy-7,8-dihydro-5(6H)-quinolinone

생성물 1

HCID 103305125,6,7,8-tetrahydro-5-oxo-1-(2-propenyl)-2(1H)-quinolinone수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
25 °C

실험 절차

A mixture of 5,6,7,8-tetrahydro-5-oxo-2(1H)-quinolinone (20.0 g), lithium hydride (1.57 g), and dimethylformamide (800 ml) was stirred for 3 hrs at 25° C., under nitrogen. 3-Bromopropene (15.5 g) was added and the mixture was stirred for an additional eighteen hrs. The redaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was triturated with petroleum ether to afford 15.7 g (63%) of 5,6,7,8-tetrahydro-5-oxo-1-(2-propenyl)-2(1H)-quinolinone.

후처리

  1. stirringthe mixture was stirred for an additional eighteen hrs
  2. concentrationThe redaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customThe residue was triturated with petroleum ether

출처 및 근거

ORD 기록
ord-827336183f5e41aa93290886ea4bc6d6
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05216164

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