Ammonium Chloride → 5-Chloro-4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamine

HRID 476359Notes

Reaction equation

HRID 476359 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[C:13]([F:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=2[Cl:19])[CH:5]=[CH:4][N:3]=1.[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[Cl:19][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)=[CH:14][C:13]([F:15])=[C:12]([NH2:16])[CH:11]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 866416872-Chloro-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine

Product 1

HCID 866416885-Chloro-4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamineYield 88%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine (0.64 g, 2.112 mmol) was dissolved in methanol (50 mL) and THF (50.0 mL). Ammonium chloride (1.130 g, 21.12 mmol) was added, followed by zinc dust (1.381 g, 21.12 mmol). The suspension stirred at room temperature for 3 hours and was then filtered through Celite® and evaporated to yield a brown solid, which was then partitioned between a 4:1 mixture of ethyl acetate and THF (150 mL) and water (75 mL). The organic layer was washed with brine, dried over magnesium sulfate, and evaporated to afford 5-chloro-4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamine (0.505 g, 88% yield) as a thick brown oil. MS (ESI) m/z: 273.0 (M+H+).

Workup

  1. filtrationwas then filtered through Celite®
  2. customevaporated
  3. customto yield a brown solid, which
  4. customwas then partitioned between a 4:1 mixture of ethyl acetate and THF (150 mL) and water (75 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-2ecbbe1377844d50b319225a13312bcd
Source dataset
uspto-grants-2014_01
Patent number
US08637672B2

Reaction notes

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