Hydrazine hydrate (1:1) → 4-Nitrobenzylamine

HRID 1428708Notes

Reaction equation

HRID 1428708 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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>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 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 291474-NitrobenzylamineYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Nitrobenzyl)isoindoline-1,3-dione (1.4 g, 4.96 mmol) was dissolved in tetrahydrofuran (8 mL). To the solution hydrazine monohydrate (1.48 mL, 19.84 mmol) and p-toluenesulfonic acid monohydrate (94 mg, 0.5 mmol) was added. It was refluxed for 6 h. TLC showed complete consumption of starting material. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give (4-nitrophenyl)methanamine (651 mg, 86%).

Workup

  1. temperatureIt was refluxed for 6 h
  2. customconsumption of starting material
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-f62e9ac3a4744fdcbd9eb06eefb3c6f1
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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