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

HRID 1005683Notes

Reaction equation

HRID 1005683 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

In ethanol (40 ml) was dissolved 2.1 g of N-acetyl-N-(3-nitrophenethyl)amine (Preparation Example 28), and powdered iron (2.25 g), ammonium acetate (4.3 g) and water (20 ml) were added thereto, followed by heating under reflux for 1.5 hours. The solid matter was filtered off and washed with ethanol, and a part of the filtrate was evaporated. The residue was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give the title compound (1.723 g, 96%) as a yellow oil.

Workup

  1. additionwere added
  2. temperatureby heating
  3. temperatureunder reflux for 1.5 hours
  4. filtrationThe solid matter was filtered off
  5. washwashed with ethanol
  6. customa part of the filtrate was evaporated
  7. extractionThe residue was extracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-49e02630b8ae4d999313e885843b385c
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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