Ammonium Chloride → HCID 67240182, compound

HRID 1028103Notes

Reaction equation

HRID 1028103 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[NH4+].[Cl-]>C(O)C.[Fe]>[NH2:8][C:6]1[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([Br:1])[CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

Product 1

HCID 67240182HCID 67240182, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

N-(3-bromo-5-nitrophenyl)acetamide (4 g, 15.44 mmol) was dissolved in ethanol (154 mL) and saturated NH4Cl(aq) (2 mL). Iron (2.59 g, 46.3 mmol) was added to the solution the reaction mixture was heated to 80° C. for 30 minutes. Upon completion, the reaction was cooled to room temperature and filtered through a short pad of silica gel (ethyl acetate wash). The organic was dried over sodium sulfate, filtered, and concentrated under reduced pressure. N-(3-amino-5-bromophenyl)acetamide was isolated as a beige foam (3.25 g, 14.19 mmol, 92%).

Workup

  1. temperatureUpon completion, the reaction was cooled to room temperature
  2. filtrationfiltered through a short pad of silica gel (ethyl acetate wash)
  3. dry with materialThe organic was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74d670a069f948b5a73a517cb08b95b9
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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