Ammonium Chloride → 3-Chloro-4-(2-pyridylmethoxy)aniline

HRID 403656Notes

Reaction equation

HRID 403656 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[Cl-].[NH4+]>C(O)C.[Fe]>[Cl:1][C:2]1[CH:15]=[C:14]([CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[NH2:16]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 174694332-((2-Chloro-4-nitrophenoxy)methyl)pyridine

Product 1

HCID 167812123-Chloro-4-(2-pyridylmethoxy)anilineYield 65.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-((2-chloro-4-nitrophenoxy)methyl)pyridine (26.5 g, 0.10 mol, 1.00 equiv), iron powder (25.2 g, 0.43 mol, 4.28 equiv) and ammonium chloride (72.24 g, 1.35 mol, 13.5 equiv) in ethanol (600 ml) was stirred mechanically under refluxed for 2 hours. The reaction was allowed to cool down; the mixture of the reaction was filtered and the filtrate was taken to dryness in vacuum. The resulted solid was dissolved in methylene chloride (500 ml) and filtered. Removal of the solvent from the filtrate in vacuum gave 15.3 g of the product. MS (ESI) m/z: 235 (M+1).

Workup

  1. temperatureunder refluxed for 2 hours
  2. temperatureto cool down
  3. additionthe mixture of the reaction
  4. filtrationwas filtered
  5. dissolutionThe resulted solid was dissolved in methylene chloride (500 ml)
  6. filtrationfiltered
  7. customRemoval of the solvent from the filtrate in vacuum

Sources & evidence

ORD record
ord-0c2e899b68294cba86c313410188ee99
Source dataset
uspto-grants-2014_06
Patent number
US08748453B2

Reaction notes

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