Acetic Acid → HCID 89103754, compound

HRID 467515Notes

Reaction equation

HRID 467515 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[N:9]=[CH:8][C:7]=1[C:20](=[O:22])[CH3:21]>CCO.O.[Fe]>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([N:10]2[C:6]([CH3:5])=[C:7]([C:20](=[O:22])[CH3:21])[CH:8]=[N:9]2)=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 28743252HCID 28743252, compound

Product 1

HCID 89103754HCID 89103754, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
75 °C

Procedure

2 ml of acetic acid and 0.64 g of iron(0) are added to 0.94 g of 1-[5-methyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl]ethanone (Journal of Chemical Research, Synopses (1986), (5), 166-7) in 60 ml of EtOH/water mixture (65/35; v/v). It is heated at 75° C. for 2 hours. It is concentrated, filtered on Celite®, the filtrate is neutralized with saturated Na2CO3 and it is extracted with DCM. The organic phase is washed with water, with brine, it is dried over Na2SO4 and evaporated. 0.70 g of yellow powder is obtained.

Workup

  1. concentrationIt is concentrated
  2. filtrationfiltered on Celite®
  3. extractionis extracted with DCM
  4. washThe organic phase is washed with water, with brine, it
  5. dry with materialis dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-b0e117b8c9cd4172a4e1f1508147bd44
Source dataset
uspto-grants-2014_01
Patent number
US08623862B2

Reaction notes

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