Ammonium Chloride → HCID 66613369, compound

HRID 2276004

Reaction equation

HRID 2276004 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:13]([CH3:14])[N:12]=[C:11]([CH3:15])[C:10]=1[N+:16]([O-])=O.[Cl-].[NH4+]>C(O)C.C(OCC)(=O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:13]([CH3:14])[N:12]=[C:11]([CH3:15])[C:10]=1[NH2:16]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 666141515-(2-chloro-4-fluorophenyl)-1,3-dimethyl-4-nitro-1H-pyrazole2×

Product 1

HCID 66613369HCID 66613369, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(2-chloro-4-fluorophenyl)-1,3-dimethyl-4-nitro-1H-pyrazole (i.e. the product of Step A) (0.2 g, 0.74 mmol), iron powder (0.2 g, 3.6 mmol) and saturated aqueous ammonium chloride solution (1 mL) in ethanol (5 mL) was heated at 80° C. for 4 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and filtered through a pad of Celite® (diatomaceous earth) on a sintered glass frit funnel. The filtrate was concentrated under reduced pressure and the resulting material was purified by silica gel column chromatography (ethyl acetate as eluant) to provide the title compound (0.14 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered through a pad of Celite® (diatomaceous earth) on a sintered glass frit funnel
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting material was purified by silica gel column chromatography (ethyl acetate as eluant)

Sources & evidence

ORD record
ord-635ba35e5dfd477badc2b076a64eff08
Source dataset
uspto-grants-2015_09
Patent number
US09131693B2

Linked notes

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