Ammonium Chloride → HCID 67184833, compound

HRID 45891Notes

Reaction equation

HRID 45891 reaction equation
BrC1C(C2C(F)=CC=C([N+]([O-])=O)C=2F)=NN(C)C=1.[Br:19][C:20]1[CH:21]=[N:22][N:23]([CH3:36])[C:24]=1[C:25]1[C:30]([F:31])=[CH:29][CH:28]=[C:27]([N+:32]([O-])=O)[C:26]=1[F:35].[Cl-].[NH4+]>O1CCOCC1.O.[Zn]>[Br:19][C:20]1[CH:21]=[N:22][N:23]([CH3:36])[C:24]=1[C:25]1[C:26]([F:35])=[C:27]([CH:28]=[CH:29][C:30]=1[F:31])[NH2:32]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 67184416HCID 67184416, compoundHCID 67184879HCID 67184879, compound

Product 1

HCID 67184833HCID 67184833, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-bromo-3-(2,6-difluoro-3-nitrophenyl)-1-methyl-1H-pyrazole and its regioisomer 4-bromo-5-(2,6-difluoro-3-nitrophenyl)-1-methyl-1H-pyrazole (0.35 g, 1.1 mmol), powdered zinc (0.39 g, 6 mmol) and ammonium chloride (0.6 g, 11 mmol) in dioxane (6 mL) and water (2 mL) were refluxed under good stirring for 3 h. After cooling, the mixture was filtered and the filtrate was concentrated. The residue was taken up with dichloromethane, washed with saturated aqueous solution of sodium hydrogen carbonate and water, dried over anhydrous sodium sulfate and concentrated. The crude mixture of 3-(4-bromo-1-methyl-1H-pyrazol-3-yl)-2,4-difluoroaniline and its regioisomer 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)-2,4-difluoroaniline was obtained as a brownish solid (0.33 g, 95%).

Workup

  1. temperaturewere refluxed
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. washwashed with saturated aqueous solution of sodium hydrogen carbonate and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. additionThe crude mixture of 3-(4-bromo-1-methyl-1H-pyrazol-3-yl)-2,4-difluoroaniline

Sources & evidence

ORD record
ord-efafc9423027483b94d8fca692f03af5
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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