Hydrazine → 2-(3-Nitrophenyl)ethan-1-amine

HRID 1005681Notes

Reaction equation

HRID 1005681 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][CH2:8][N:9]1C(=O)C2=CC=CC=C2C1=O)([O-:3])=[O:2].NN>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][CH2:8][NH2:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22674056N-(3-nitrophenethyl)phthalimide

Product 1

HCID 129500662-(3-Nitrophenyl)ethan-1-amineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (150 ml) was suspended N-(3-nitrophenethyl)phthalimide obtained in Preparation Example 26. To the mixture was added hydrazine (5.7 ml), followed by heating under reflux for 1 hour. Though the reaction mixture was once completely dissolved, crystals again precipitated. The crystals were filtered off and washed with cooled ethanol. Then, the solvent was evaporated, to give the title compound (5.559 g, 99%) as a yellow oil.

Workup

  1. customobtained in Preparation Example 26
  2. temperatureby heating
  3. temperatureunder reflux for 1 hour
  4. dissolutionThough the reaction mixture was once completely dissolved
  5. customcrystals again precipitated
  6. filtrationThe crystals were filtered off
  7. washwashed with cooled ethanol
  8. customThen, the solvent was evaporated

Sources & evidence

ORD record
ord-4bc13e98c024488d9842512536d09b38
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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