Hydrochloric Acid → 6-Methoxy-7-nitroindoline-2,3-dione

HRID 1398956ノート

反応式

HRID 1398956 の反応式
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]2[C:5]([C:6](=[O:15])[C:7](=[O:14])[NH:8]2)=[CH:4][CH:3]=1.[CH3:16][O-:17].[Na+].Cl>CO>[CH3:16][O:17][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]2[C:5]([C:6](=[O:15])[C:7](=[O:14])[NH:8]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 687738666-chloro-7-nitro-1H-indole-2,3-dione

生成物 1

HCID 137922426-Methoxy-7-nitroindoline-2,3-dione収率 69%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of 6-chloro-7-nitro-1H-indole-2,3-dione (2.0 g, 8.83 mmol) in methanol (20 mL) was added a solution of sodium methoxide in methanol (28%, 3.8 mL) at room temperature. The mixture was stirred at 60° C. for 14 hr. 1N Hydrogen chloride (10 mL) was added to the reaction mixture at 0° C. and the mixture was extracted with ethyl acetate. The organic layer was washed with brine (×3), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 30-100% ethyl acetate/n-hexane gradient mixture to give the title compound (1.349 g, 6.07 mmol, 69%) as a yellow solid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine (×3)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 30-100% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-0069d2056a2547ac884c7891e9b7326d
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

読み込み中…