Acetic Acid → HCID 86710576, compound

HRID 1027181Notes

Reaction equation

HRID 1027181 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[N:9]2)=[CH:4][C:3]=1[O:16][CH3:17].C(O)(=O)C>C(Cl)Cl.C1(C)C=CC=CC=1.[Zn]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([NH2:13])=[N:9]2)=[CH:4][C:3]=1[O:16][CH3:17]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 86710575HCID 86710575, compound

Product 1

HCID 86710576HCID 86710576, compoundYield 91.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(4-bromo-3-methoxyphenyl)-3-nitro-1H-pyrazole (2.3 g, 7.72 mmol) in DCM (24 mL) and acetic acid (6.18 mL, 108 mmol) was added zinc dust (2.52 g, 38.6 mmol) at 0° C. The reaction mixture was stirred at 0° C. to RT overnight. The reaction mixture was filtered through celite, rinsed with EtOAc and concentrated in vacuo. The residue was purified by silica chromatography (EtOAc/heptane=10:90 to 50:50) to give a white foam which was dissolved in 6 mL of toluene, concentrated and dried to give 1.9 g of 1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-3-amine as a white powder.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washrinsed with EtOAc
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica chromatography (EtOAc/heptane=10:90 to 50:50)
  5. customto give a white foam which
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-68525ba7770849eb8e4c94c712df2d82
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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