Hydrochloric Acid → 7-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazin-2-one

HRID 255377ノート

反応式

HRID 255377 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N+:15]([O-])=O)[C:5]([O:8][CH2:9][C:10](OCC)=[O:11])=[N:6][CH:7]=1.Cl.[Sn](Cl)(Cl)(Cl)Cl.CO.C(Cl)(Cl)Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[O:8][CH2:9][C:10](=[O:11])[NH:15][C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24287Tin tetrachlorideHCID 4647502Ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetate2 回HCID 21584188Chloroform methanol

生成物 1

HCID 45901417-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazin-2-one収率 37.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

Ethyl [(5-bromo-3-nitropyridin-2-yl)oxy]acetate (intermediate 212) (4.3 g, 14.1 mmol) was dissolved in anhydrous THF (10 mL) and concentrated HCl (10 mL) was added at 0° C. Tin chloride (5.0 g, 26.4 mmol) was added in small portions. The reaction was stirred for 1 hr and heated at 65° C. overnight. The reaction mixture was concentrated under reduced pressure, extracted with chloroform, dried over magnesium sulfate and concentrated. Chromatography on silica gel with methanol/chloroform gave the product as a light pink solid (1.2 g, 37% yield).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with chloroform
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-70393ca5d06944129a8f7c2be6e79f0d
出典データセット
uspto-grants-2011_01
特許番号
US07875715B2

反応ノート

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