Ammonium Chloride → 5-bromo-N-(4-methoxybenzyl)benzene-1,2-diamine

HRID 1051452Notes

Reaction equation

HRID 1051452 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-])=O)=[C:6]([CH:17]=1)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[Cl-].[NH4+]>CCO.O.[Fe]>[Br:1][C:2]1[CH:17]=[C:6]([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([NH2:18])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 653416735-bromo-N-(4-methoxybenzyl)-2-nitroaniline

Product 1

HCID 653433435-bromo-N-(4-methoxybenzyl)benzene-1,2-diamineYield 82%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-N-(4-methoxybenzyl)-2-nitroaniline (750 mg, crude) in EtOH (8 mL) and H2O (8 mL) was added Fe powder (766 mg, 13.7 mmol) and ammonium chloride (733 mg, 13.7 mmol). The mixture was stirred at 60° C. for 4 h then filtered and the filtrate was concentrated to remove EtOH. The residue was then diluted with water and extracted with EtOAc. The organic layer was concentrated to give the desired product (550 mg, crude, 82% yield) with the crude product being used in next step without further purification. LCMS (m/z): 308.1 [M+H]+

Workup

  1. filtrationthen filtered
  2. concentrationthe filtrate was concentrated
  3. customto remove EtOH
  4. additionThe residue was then diluted with water
  5. extractionextracted with EtOAc
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-775cbc0f420d4bb5b41722793be9a91d
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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