Ammonium Chloride → 5-Bromo-N1-methylbenzene-1,2-diamine

HRID 1507023Notes

Reaction equation

HRID 1507023 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[NH:7][CH3:8].[Cl-].[NH4+]>CCO.O.[Fe]>[Br:1][C:2]1[CH:9]=[C:6]([NH:7][CH3:8])[C:5]([NH2:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 106095305-bromo-N-methyl-2-nitroaniline

Product 1

HCID 121982705-Bromo-N1-methylbenzene-1,2-diamineYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-N-methyl-2-nitroaniline (10 g, 43.5 mmol) in EtOH/H2O (700 mL) was added Fe (14.6 g, 261 mmol), ammonium chloride (14 g, 261 mmol) and the reaction mixture was heated at 60° C. for 4 h. The crude reaction mixture was filtered, concentrated, dissolved in ethyl acetate, washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was used in next reaction without further purification. (7.9 g, yield 90%) MS (ESI+) e/z: 202.1.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was used in next reaction without further purification

Sources & evidence

ORD record
ord-12262510dc7d4416a53651014ada250b
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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