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

HRID 656941

反応式

HRID 656941 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)].

後処理

  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

出典と根拠

ORDレコード
ord-4552e6b93cb24edeb2e5d73173959c23
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

関連ノート

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