Water → N-Acetyl-N-(3-aminophenethyl)amine

HRID 1173126Notes

Reaction equation

HRID 1173126 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)(=[O:3])[CH3:2].C([O-])(=O)C.[NH4+].O>C(O)C.[Fe]>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 22674066N-(3-Nitrophenethyl)acetamide

Product 1

HCID 22674097N-Acetyl-N-(3-aminophenethyl)amineYield 96%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

N-Acetyl-N-(3-nitrophenethyl)amine (2.1 g, Production Example 28b) was dissolved in ethanol (40 ml). To the mixture were added an iron powder (2.25 g), ammonium acetate (4.3 g) and water (20 ml), followed by heating under reflux for 1.5 hours. Solid was filtered off and washed with ethanol, and then the filtrate was partially evaporated. The residue was extracted with ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, to give the title compound (1.723 g, 96%) as a yellow oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. filtrationSolid was filtered off
  4. washwashed with ethanol
  5. customthe filtrate was partially evaporated
  6. extractionThe residue was extracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-af677a9849a940ed8aff78446c6cbdf0
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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