Isatoic Anhydride → 2-amino-N-(4-fluorophenyl)benzamide

HRID 1846278

反応式

HRID 1846278 の反応式
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]12[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:14]C(=O)O[C:10]2=[O:11]>CN(C)C=O.C(OCC)(=O)C>[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=1[C:10]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)=[O:11]

参加物

5

反応物 2

HCID 8359Isatoic AnhydrideHCID 97314-Fluoroaniline

生成物 1

HCID 4788222-amino-N-(4-fluorophenyl)benzamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
115 °C

実験手順

To a solution of 4-fluoroaniline (2.40 mL, 24.5 mmol) in N,N-dimethylformamide (30 mL) was added isatoic anhydride (4.00 g, 24.5 mmol), and the reaction mixture was heated at 115° C. for 14 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (100 mL). The organic layer was washed with 1 N NaOH (200 mL), water (100 mL), then brine, and dried over Na2SO4. The solvent was removed under reduced pressure to give crude product, which was purified by column chromatography (silica gel 230-400 mesh; 10% EtOAc/hexane as eluent) to give 2-amino-N-(4-fluoro-phenyl)-benzamide as white solid. Yield: 2.00 g (35%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with 1 N NaOH (200 mL), water (100 mL)
  3. dry with materialbrine, and dried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customto give crude product, which
  6. customwas purified by column chromatography (silica gel 230-400 mesh; 10% EtOAc/hexane as eluent)

出典と根拠

ORDレコード
ord-561afb952a3f4ecdaddd8828deba7729
出典データセット
uspto-grants-2015_02
特許番号
US08952021B2

関連ノート

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