Ammonium Chloride → HCID 67184547, compound

HRID 45816Notes

Reaction equation

HRID 45816 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)=[N:5]1.[Cl-].[NH4+]>[Zn].O1CCOCC1.O>[F:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[C:6]([C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=2)[NH2:21])=[N:5]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67185846HCID 67185846, compound

Product 1

HCID 67184547HCID 67184547, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To 4-[1-(2-fluoroethyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine in a solution of dioxane/water (5:1) ammonium chloride (144 mg, 2.7 mmol) and zinc (70 mg, 1.08 mmol) were added. The reaction was stirred at 80° C. After two hours the reaction was allowed to cool to room temperature and it was poured into Na2HPO4 (pH=8) solution and extracted with ethyl acetate. The organic layer was washed with brine (1×50 mL), dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and it was used in the next step without further purification.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine (1×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure and it
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-88100f680e8d44ab9b291091f280021c
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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