Water → N-(2-nitrophenyl)benzo[d][1,3]dioxol-5-ylamine

HRID 240357

反応式

HRID 240357 の反応式
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([NH2:20])=[CH:19][C:14]=2[O:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:20][C:18]1[CH:17]=[CH:16][C:15]2[O:11][CH2:12][O:13][C:14]=2[CH:19]=1)([O-:10])=[O:9]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 843101,3-Benzodioxol-5-amine

生成物 1

HCID 7922985N-(2-nitrophenyl)benzo[d][1,3]dioxol-5-ylamine収率 65%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

9.3 g (66 mmol) of 2-fluoro-nitrobenzene and 10 g (73 mmol) of benzo[d][1,3]dioxol-5-ylamine were dissolved in N,N-dimethylformamide (60 mL) and 10.9 g (79 mmol) of potassium carbonate was added thereto. Mixed solution was heated to reflux for 10 hours while stirring. The reaction mixture was poured into water, and extracted with ethyl acetate. The extracted organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=1:3), to obtain 11 g (yield: 65%) of N-(2-nitrophenyl)benzo[d][1,3]dioxol-5-ylamine as red-purple crystals.

後処理

  1. temperatureMixed solution was heated
  2. temperatureto reflux for 10 hours
  3. extractionextracted with ethyl acetate
  4. washThe extracted organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=1:3)

出典と根拠

ORDレコード
ord-f1fb9eb241d44644a3b04aaab9f9df7e
出典データセット
uspto-grants-2014_02
特許番号
US08648075B2

関連ノート

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