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

HRID 1195169ノート

反応式

HRID 1195169 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

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 reaction 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.

後処理

  1. stirringthe mixture was stirred for an additional eighteen hrs
  2. concentrationThe reaction 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

出典と根拠

ORDレコード
ord-a4b362ce64c4468e9da61ff3a9e5d7dc
出典データセット
uspto-grants-1992_05
特許番号
US05110815

反応ノート

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