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Ethanol → Ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide

HRID 1817312
ノート
印刷プレビュー

反応式

HRID 1817312 の反応式
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:12][CH:11]=[C:10]([OH:22])[C:9]=3[C:8]2=[O:23])=[CH:4][CH:3]=1.C([OH:28])C>C(O)(=O)C>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([OH:22])[CH:11]=[N+:12]([O-:28])[C:13]=3[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8]2=[O:23])=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 702EthanolHCID 69061030Ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

生成物 1

HCID 69064622Ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

To ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (0.5 gm, 1.09 mmol; see Example 8, Step 4) in glacial acetic acid (25 mL) at room temperature under nitrogen was added, with stirring, aqueous peroxide (30% by wt) (1.24 mL, 10.9 mmol). The reaction was warmed to 100° C. and stirred for 1.5 hours. The reaction was allowed to cool, ethanol (1 mL) was added and volatile components were removed under reduced pressure. The resulting oil was placed under high vacuum for 16 hours, then used as is. Alternatively, after cooling, water can be added and the volatile components removed under reduced pressure. The residue can be partitioned between CHCl3 and saturated Na2SO3. The organic extract can be dried with Na2SO4, filtered, and concentrated under vacuum to provide the title compound.

後処理

  1. stirringstirred for 1.5 hours
  2. temperatureto cool
  3. customvolatile components were removed under reduced pressure
  4. temperatureAlternatively, after cooling
  5. additionwater can be added
  6. customthe volatile components removed under reduced pressure
  7. customThe residue can be partitioned between CHCl3 and saturated Na2SO3
  8. extractionThe organic extract can
  9. dry with materialbe dried with Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-30801494cb8b49769e24b44f48b95e72
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07598264B2

反応ノート

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