Formic Acid → HCID 19786355, compound

HRID 1030010Notes

Reaction equation

HRID 1030010 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[CH:4][C:3]=1[C:19]#N.C(O)=[O:22]>[Ni]>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[CH:4][C:3]=1[CH:19]=[O:22]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 135618335-Amino-4-cyano-1-(2-chloro-4-trifluoromethoxy-phenyl)-pyrazole

Product 1

HCID 19786355HCID 19786355, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

12 g (0.042 mol) of 5-amino-4-cyano-1-(2-chloro-4-trifluoromethoxy-phenyl)-pyrazole are boiled under reflux with 5 g of Raney nickel in 50 ml of 75% strength aqueous formic acid for 1 hour; the still warm solution is filtered under suction, the residue is rinsed with water, the filtrate is extracted several times with ether, and the combined ether phases are washed with saturated sodium bicarbonate solution, dried over sodium sulphate and evaporated down in vacuo. 8.0 g (62% of theory) of 5-amino-1-(2-chloro-4-trifluoromethoxy-phenyl)-4-formylpyrazole are obtained in the form of an oil.

Workup

  1. filtrationthe still warm solution is filtered under suction
  2. washthe residue is rinsed with water
  3. extractionthe filtrate is extracted several times with ether
  4. washthe combined ether phases are washed with saturated sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated down in vacuo

Sources & evidence

ORD record
ord-bd3a9e71f6b54361bd3c15ffa59e55d4
Source dataset
uspto-grants-1992_04
Patent number
US05104439

Reaction notes

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