반응 #1605822

ord-973ea9e53b9a48198face942c0e6fa1a

반응 방정식

COc1ccc(COc2ccc(C(C)=O)c3ccc(=O)[nH]c23)cc1
5-Acetyl-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one
[Br-].[Br-].[Br-].c1cc[nH+]cc1.c1cc[nH+]cc1.c1cc[nH+]cc1
Pyridinium tribromide
COc1ccc(COc2ccc(C(=O)CBr)c3ccc(=O)[nH]c23)cc1
5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one
수율 33.1%

반응 조건

온도
0°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도the reaction mixture was heated
  2. 2
    온도under reflux overnight
  3. 3
    여과The precipitate was collected by filtration
  4. 4
    세척washed with tetrahydrofuran
  5. 5
    농축The filtrate was concentrated under reduced pressure
  6. 6
    세척the residue was suspension-washed with purified water (20 mL)
  7. 7
    여과The precipitate was collected by filtration
  8. 8
    세척washed with purified water
  9. 9
    세척The solid was suspension-washed with ethyl acetate (20 mL)
  10. 10
    여과collected by filtration
  11. 11
    기타dried under reduced pressure

실험 절차

5-Acetyl-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (1.25 g, 3.87 mmol) was dissolved in tetrahydrofuran (10 mL) and the solution was cooled to 0° C. Pyridinium tribromide (1.51 g, 4.25 mmol) was added in portions thereto and the reaction mixture was heated under reflux overnight. The precipitate was collected by filtration and washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure and, thereafter, the residue was suspension-washed with purified water (20 mL). The precipitate was collected by filtration and washed with purified water. The solid was suspension-washed with ethyl acetate (20 mL), collected by filtration, and dried under reduced pressure to obtain 5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (515 mg).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09072734B2uspto-grants-2015_07