Butanamide, N-(3-nitrophenyl)- → N-(3-aminophenyl)butanamide

HRID 1484536Notes

Reaction equation

HRID 1484536 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:15])[CH2:12][CH2:13][CH3:14])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:15])[CH2:12][CH2:13][CH3:14])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 346258Butanamide, N-(3-nitrophenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 721132N-(3-aminophenyl)butanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(3-nitrophenyl)butyramide (8.60 g, 41.3 mmol) in MeOH (207 mL) was divided between two 500 mL flasks with stir bars. Each flask was flushed well with nitrogen, then 5% palladium on carbon (4.40 g, 2.065 mmol) was added, half to each flask. A 3-way adapter with a large hydrogen-filled balloon was attached to each flask, and the reactions were evacuated and back-filled with hydrogen five times, while stirring vigorously. The reactions were then stirred for 16 h, then filtered through a funnel packed with Celite. The filter cake was washed with MeOH, and the filtrate was concentrated, redissolved with DCM, then purified by column chromatography (EtOAc/hexanes gradient) to yield a white solid after precipitating from hexanes (5.87 g, 80%). LRMS (ESI+) (M+H): 179.18.

Workup

  1. customEach flask was flushed well with nitrogen
  2. customwas attached to each flask
  3. customthe reactions were evacuated
  4. additionback-filled with hydrogen five times
  5. stirringThe reactions were then stirred for 16 h
  6. filtrationfiltered through a funnel
  7. washThe filter cake was washed with MeOH
  8. concentrationthe filtrate was concentrated
  9. dissolutionredissolved with DCM
  10. custompurified by column chromatography (EtOAc/hexanes gradient)
  11. customto yield a white solid
  12. customafter precipitating from hexanes (5.87 g, 80%)

Sources & evidence

ORD record
ord-ab42e9e2b73b467ea7ee1bb02c5702d7
Source dataset
uspto-grants-2016_08
Patent number
US09422262B2

Reaction notes

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