Ammonium Chloride → N-(2-Amino-6-bromophenyl)acetamide

HRID 1270399Notes

Reaction equation

HRID 1270399 reaction equation
[Cl-].[NH4+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[NH:13][C:14](=[O:16])[CH3:15]>C(O)C.O.CN(C=O)C.[Fe]>[NH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([Br:3])[C:5]=1[NH:13][C:14](=[O:16])[CH3:15]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 4643062N-(2-bromo-6-nitrophenyl)acetamide

Product 1

HCID 18449402N-(2-Amino-6-bromophenyl)acetamide

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Iron powder (2.92 g, 52.32 mmol) and ammonium chloride (2.3 g, 43.6 mmol) in ethanol (40 mL) and water (20 mL) were added to a solution of N-(2-bromo-6-nitrophenyl)acetamide [Edlin et al., New Journal of Chemistry 1999, 23, 819–826] (2.26 g, 8.72 mmol) in DMF (20 mL) and the mixture was heated at reflux. After 6 h, the reaction was filtered through a celite pad, washed with acetone, and concentrated in vacuo to give the title compound. MS: m/z=231 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. filtrationthe reaction was filtered through a celite pad
  4. washwashed with acetone
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ebc565b390a485dbab06d91a7d24232
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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