Hydrazine hydrate (1:1) → 4-Nitrobenzylamine

HRID 1428764Notes

Reaction equation

HRID 1428764 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 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Nitrobenzyl)isoindoline-1,3-dione (1.6 g, 5.67 mmol) was dissolved in tetrahydrofuran (8 mL). To the solution hydrazine monohydrate (1.7 mL, 22.675 mmol) and p-toluenesulfonic acid monohydrate (108 mg, 0.57 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 (715 mg, 83%).

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-7abdfe653f384a58aedd363ed945756c
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

Loading…