HCID 57555196, compound → HCID 57555342, compound

HRID 220760Notes

Reaction equation

HRID 220760 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:22])[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[N+:19]([O-])=O)=[O:5])[CH3:2]>CO.C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:22])[C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[NH2:19])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 57555196HCID 57555196, compound

Product 1

HCID 57555342HCID 57555342, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

Zinc powder (26.17 g, 400 mmol) was added to a suspension of 5-(4-chloro-2-nitro-phenylamino)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester from Example E1.1 (26.0 g, 80 mmol) in methanol/acetic acid (10:1, 330 ml) at room temperature. After the exothermic reaction which followed, the resulting suspension was stirred at room temperature for 18 h before being filtered through Celite® filter agent. The filtrate was concentrated in vacuo. The residue was dissolved in EtOAc, and the solution was washed with saturated NaHCO3 and brine, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 65% EtOAc:35% pet ether to 80% EtOAc:20% pet ether) to yield the title compound (18.41 g, 78.0%).

Workup

  1. customAfter the exothermic reaction which
  2. filtrationbefore being filtered through Celite®
  3. filtrationfilter agent
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washthe solution was washed with saturated NaHCO3 and brine
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (eluant; 65% EtOAc:35% pet ether to 80% EtOAc:20% pet ether)

Sources & evidence

ORD record
ord-b98f54275a974514a8b07cd86ab53a7a
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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