Ammonium Chloride → 4-Benzyloxy-3-chloroaniline

HRID 1013914

Reaction equation

HRID 1013914 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[Cl:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[Cl:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 3085094-Benzyloxy-3-chloronitrobenzene

Product 1

HCID 12682854-Benzyloxy-3-chloroanilineYield 95.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 6.59 g (0.025 moles) of the 4-benzyloxy-3-chloro nitrobenzene (example 4), 4.19 g (0.075 moles) of iron powder, and 12.04 g (0.225 moles) of ammonium chloride in 100 ml of ethanol and 25 ml of water was stirred mechanically and refluxed for half an hour. The reaction was allowed to cool and stir for 1 hour. The mixture was filtered and solids were washed with ethanol. The combined filtrates were taken to dryness in vacuo. This solid was dissolved in methylene chloride and passed through Magnesol. Removal of the solvent from the filtrate in vacuo gave 5.60 g of title compound.

Workup

  1. temperaturerefluxed for half an hour
  2. temperatureto cool
  3. stirringstir for 1 hour
  4. filtrationThe mixture was filtered
  5. washsolids were washed with ethanol
  6. dissolutionThis solid was dissolved in methylene chloride
  7. customRemoval of the solvent from the filtrate in vacuo

Sources & evidence

ORD record
ord-78882305ae6a446baa474dc23978d36c
Source dataset
uspto-grants-2011_07
Patent number
US07982043B2

Linked notes

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