Hydrazine → 4-(diethylaminomethyl)aniline

HRID 2352990Notes

Reaction equation

HRID 2352990 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].NN>[Ni].C(O)C>[CH2:1]([N:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 412435N-ethyl-N-[(4-nitrophenyl)methyl]ethanamine

Product 1

HCID 2368034-(diethylaminomethyl)anilineYield 91.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a suspension of N-ethyl-N-(4-nitrobenzyl)ethanamine (335 mg, 1.61 mmol) and Raney Ni (50 mg) in refluxing ethanol (10 mL) was added drop-wise anhydrous hydrazine (0.5 mL). After the addition was complete, the mixture was refluxed for an additional 20 minutes and then filtered through a pad of Celite. The Celite bed was washed with ethanol (100 mL) and the combined solution was evaporated under reduced pressure to provide pure 4-((diethylamino)methyl)aniline (262 mg, 91%).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for an additional 20 minutes
  3. filtrationfiltered through a pad of Celite
  4. washThe Celite bed was washed with ethanol (100 mL)
  5. customthe combined solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a2b8a0308e2f48a3ae12ec11c03d0663
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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