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

HRID 1428737Notes

Reaction equation

HRID 1428737 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-bebf7feec8c84bc3b6d3989b0603f1b6
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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