Allyl iodide → 7-fluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinone

HRID 656941노트

반응식

HRID 656941 반응식
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.F[C:14]1[CH:15]=C2C(=C[CH:23]=1)NC(=O)C=N2.C(=O)([O-])[O-].[K+].[K+].C(I)C=C>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:12])[N:9]2[CH2:15][CH:14]=[CH2:23])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 126863866-Fluoro-1,2-dihydroquinoxalin-2-oneHCID 217275347-fluoroquinoxalin-2(1H)-one

생성물 1

HCID 688167377-fluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A 1:2 mixture of 7-fluoro-2(1H)-quinoxalinone and 6-fluoro-2(1H)-quinoxalinone (20 g, 0.122 mol) in dry DMF (250 ml) and anhydrous potassium carbonate (50.5 g, 0.38 mol) was treated with allyl iodide (12.3 ml, 0.134 mol) and the mixture was stirred at rt for 2 hours. The reaction mixture was evaporated to dryness, water was added and the mixture was extracted (3×) with DCM, washed with water, dried (sodium sulphate) and evaporated. It was chromatographed, twice, on silica gel, eluting with 0-40% ethyl acetate-hexane. The early fractions gave 7-fluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinone (4.7 g) [later fractions contained the isomeric 6-fluoro-isomer (6.7 g)].

후처리

  1. customThe reaction mixture was evaporated to dryness, water
  2. additionwas added
  3. extractionthe mixture was extracted (3×) with DCM
  4. washwashed with water
  5. dry with materialdried (sodium sulphate)
  6. customevaporated
  7. customIt was chromatographed
  8. washtwice, on silica gel, eluting with 0-40% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-4552e6b93cb24edeb2e5d73173959c23
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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