N-((4-Nitrophenyl)methyl)acetamide → N-(4-AMINO-BENZYL)-ACETAMIDE

HRID 552121Notes

Reaction equation

HRID 552121 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][NH:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C1COCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10](=[O:12])[CH3:11])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 41784N-((4-Nitrophenyl)methyl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 228286N-(4-AMINO-BENZYL)-ACETAMIDEYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.0 g (21 mmol, 1.0 eq.) of N-(4-nitrobenzyl)acetamide (I-21) in 100 mL of THF was added a catalytic amount of Raney Nickel. The mixture was stirred under 1 atm. of hydrogen at room temperature for 16 h. The mixture was filtered through Celite® and the pad was washed with 100 mL of THF. The solvent was removed in vacuo to provide 3.4 g (21 mmol, 100%) of N-(4-aminobenzyl)acetamide (I-22).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe pad was washed with 100 mL of THF
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-146d079e255f45ee93e4a7ebdedac062
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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