Hydrazine hydrate (1:1) → 4-Nitrobenzylamine

HRID 1428775Notes

Reaction equation

HRID 1428775 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O.NN.C(=O)(O)[O-].[K+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH2:9])=[CH:20][CH:21]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 2708672-(4-Nitro-benzyl)-isoindole-1,3-dioneHCID 516893Potassium Bicarbonate

Product 1

HCID 291474-NitrobenzylamineYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-nitrobenzyl)isoindoline-1,3-dione (1.6 g, 5.33 mmol) in tetrahydrofuran was added hydrazine monohydrate (4 eq). The mixture was refluxed for 6 h. After cooling down to room temperature the mixture was treated with potassium bicarbonate to pH 12˜13, extracted with ethyl acetate and washed with brine. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave (4-nitrophenyl)methanamine (592 mg, 65%).

Workup

  1. temperatureThe mixture was refluxed for 6 h
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialDrying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography

Sources & evidence

ORD record
ord-9577714ba0d245e38d01c340107adbc1
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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