Hydrogen Bromide → 8-Ethyl-7-fluoro-1,5-naphthyridin-2(1H)-one

HRID 656903ノート

反応式

HRID 656903 の反応式
[CH2:1]([C:3]1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13]C)[CH:9]=[CH:8]2)[CH3:2].Br.C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[CH2:1]([C:3]1[C:4]([F:15])=[CH:5][N:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH:9]=[CH:8]2)[CH3:2]

参加物

6

反応物 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 671312018-Ethyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine

生成物 1

HCID 688187718-Ethyl-7-fluoro-1,5-naphthyridin-2(1H)-one収率 83.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒

実験手順

A suspension of 8-ethyl-7-fluoro-2-(methyloxy)-1,5-naphthyridine (1.045 g, 5.07 mmol) in glacial acetic acid (10 ml) at rt under argon, was treated with 33% HBr in acetic acid (10 mL). After stirring at rt for 18 h, the solvents were evaporated under reduced pressure. More glacial acetic acid (10 ml) was added to the reaction mixture and the solvent was removed to give a yellow solid. As this residue was placed in water (ca. 50 ml) a white precipitate came out of solution. The pH was adjusted to pH 6-7 by addition of solid sodium hydrogen carbonate. The mixture was then stirred at rt for 2 h, after which the solid was isolated by filtration with suction to give a white damp solid. This product was dried on the sinter with suction for 2 h then dried in a vacuum oven over 18 h at 40° C. to give the title compound as an white solid (0.81 g, 83%).

後処理

  1. customthe solvents were evaporated under reduced pressure
  2. additionMore glacial acetic acid (10 ml) was added to the reaction mixture
  3. customthe solvent was removed
  4. customto give a yellow solid
  5. stirringThe mixture was then stirred at rt for 2 h
  6. customafter which the solid was isolated by filtration with suction
  7. customto give a white damp solid
  8. customThis product was dried on the sinter with suction for 2 h
  9. customthen dried in a vacuum oven over 18 h at 40° C.

出典と根拠

ORDレコード
ord-f6f620c403094464a135442422787344
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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