Ammonium Chloride → N1-benzyl-5-bromobenzene-1,2-diamine

HRID 1051466Notes

Reaction equation

HRID 1051466 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH2:1]([NH:8][C:9]1[C:10]([NH2:16])=[CH:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 24902978N-benzyl-5-bromo-2-nitroaniline

Product 1

HCID 65343042N1-benzyl-5-bromobenzene-1,2-diamine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-benzyl-5-bromo-2-nitroaniline (700 mg, 2.28 mmol) in EtOH (8 mL) and water (8 mL) was added iron powder (766 mg, 13.7 mmol) and NH4Cl (733 mg, 13.7 mmol). The mixture was stirred at 60° C. for 4 h. The reaction solution was filtered with the filtrate concentrated to remove EtOH. The residue was diluted with water and extracted with EtOAc with the organic layer concentrated to give the crude N1-benzyl-5-bromobenzene-1,2-diamine. The crude product was used in next step without further purification. LCMS (m/z): 277.1/278.1 [M+H]+/[M+2H]+

Workup

  1. filtrationThe reaction solution was filtered with the filtrate
  2. concentrationconcentrated
  3. customto remove EtOH
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc with the organic layer
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3e1ea6a0f444442db0bcfc26bf812e30
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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