Hydrazine hydrate (1:1) → (2-Fluoro-4-nitrophenyl)methanamine

HRID 1428737노트

반응식

HRID 1428737 반응식
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.O.NN.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:3]=1[CH2:4][NH2:5]

참가 물질

6

반응물 3

HCID 24654Hydrazine hydrate (1:1)HCID 521998p-Toluenesulfonic acid monohydrateHCID 708476692-(2-Fluoro-4-nitrobenzyl)isoindoline-1,3-dione

생성물 1

HCID 45121148(2-Fluoro-4-nitrophenyl)methanamine수율 68.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 2-(2-fluoro-4-nitrobenzyl)isoindoline-1,3-dione (500 mg, 1.665 mmol) in tetrahydrofuran were added hydrazine monohydrate (333 mg, 6.661 mmol) and p-toluenesulfonic acid monohydrate (29 mg, 0.167 mmol). The reaction mixture was refluxed for 6 h, then cooled to room temperature, diluted with ethyl acetate. The mixture was washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography to give (2-fluoro-4-nitrophenyl)methanamine (194 mg, 68%).

후처리

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. washThe mixture was washed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was removed in vacuo
  6. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-bebf7feec8c84bc3b6d3989b0603f1b6
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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