HCID 91659208, compound → 2-Amino-4-bromo-5-chlorobenzamide

HRID 588906Notes

Reaction equation

HRID 588906 reaction equation
[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([N+:12]([O-])=O)[CH:3]=1>CC(O)=O.O.[Fe]>[NH2:12][C:4]1[CH:3]=[C:2]([Br:1])[C:10]([Cl:11])=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7]

Participants

5

Reactant 1

HCID 91659208HCID 91659208, compound

Product 1

HCID 916592092-Amino-4-bromo-5-chlorobenzamideYield 97%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromo-5-chloro-2-nitrobenzamide (900 mg, 3.2 mmol) in AcOH (20 mL) and water (5 mL) at 70° C., Fe powder (900 mg, 16.1 mmol) was added and the resulting mixture was stirred at 70° C. for 1 h. The mixture was allowed to cool to RT and poured into ice-water. The precipitate was collected by filtration and rinsed with water. This crude product was dissolved with ethyl acetate and filtered. The filtrate was washed with saturated NaHCO3 solution and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product (770 mg, 97% yield). ESI-MS m/z: 250.1[M+H]+.

Workup

  1. temperatureto cool to RT
  2. filtrationThe precipitate was collected by filtration
  3. washrinsed with water
  4. dissolutionThis crude product was dissolved with ethyl acetate
  5. filtrationfiltered
  6. washThe filtrate was washed with saturated NaHCO3 solution and brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ea1f7c3684347c8a336edfcfdd72eb3
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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