Ammonium Chloride → 3-Chloro-4-(3-fluorobenzyloxy)aniline

HRID 38507

Reaction equation

HRID 38507 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1.[Cl-].[NH4+]>C(O)C.O.[Zn]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[NH2:8]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 70592692-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzene

Product 1

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineYield 120.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-1-[(3-fluorobenzyl)oxy]-4-nitrobenzene from Example 3A (8.70 g, 25.1 mmol) in ethanol (150 mL) was added zinc powder (10.1 g, 154 mmol), and the mixture was heated to 60° C. A solution of ammonium chloride (3.30 g, 61.8 mmol) in water (30 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 7.63 g (98%) 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-dd81d357f3de43e5a595a46905d3e911
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

Loading…