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

HRID 38509

Reaction equation

HRID 38509 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.O.[Zn]>[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

6

Reactant 2

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

Product 1

HCID 167812123-Chloro-4-(2-pyridylmethoxy)anilineYield 84.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[(2-chloro-4-nitrophenoxy)methyl]pyridine from Example 5A (6.65 g, 25.1 mmol) in ethanol (120 mL) was added zinc powder (8.22 g, 126 mmol), and the mixture was heated to 60° C. A solution of ammonium chloride (2.67 g, 50.3 mmol) in water (24 mL) was added dropwise, and the reaction was stirred for additional 2 h at this temperature. The mixture was filtered through Celite®, and the solvent was removed in vacuo. The residue was triturated with water, and the precipitate was collected by suction filtration, washed with water and dried to yield 4.97 g (84%) of the aniline.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customthe solvent was removed in vacuo
  3. customThe residue was triturated with water
  4. filtrationthe precipitate was collected by suction filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-6ae58217c57a49c680c248046ffadf6a
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

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