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

HRID 1846278

반응식

HRID 1846278 반응식
[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]

참가 물질

5

반응물 2

HCID 8359Isatoic AnhydrideHCID 97314-Fluoroaniline

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
115 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-561afb952a3f4ecdaddd8828deba7729
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952021B2

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