Hydrazine hydrate (1:1) → HCID 57441034, compound

HRID 2391144Notes

Reaction equation

HRID 2391144 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)=[O:8])=[CH:5][C:4]([CH3:19])=[N:3]1.O.NN>C(O)C.[Pd]>[NH2:16][C:12]1[CH:11]=[C:10]([NH:9][C:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([CH3:19])[CH:5]=2)=[O:8])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 16953136HCID 16953136, compound

Product 1

HCID 57441034HCID 57441034, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-nitroaniline (1.0 g, 7.2 mmol) in N,N-dimethylacetamide (6 mL) was added a solution of 1,3-dimethyl-1H-pyrazole-5-carbonylchloride (1260 mg, 8.0 mmol) in N,N-dimethylacetamide (2 mL), and the mixture was stirred at room temperature for 30 min. Water (200 mL) was added to the mixture under ice-cooling, and the mixture was filtrated. The obtained solid was washed with water and diethyl ether to give 1,3-dimethyl-N-(3-nitrophenyl)-1H-pyrazole-5-carboxamide (1850 mg, 7.1 mmol). To a solution of the obtained 1,3-dimethyl-N-(3-nitrophenyl)-1H-pyrazole-5-carboxamide (1850 mg, 7.1 mmol) in ethanol (50 mL) was added 10% palladium/carbon (190 mg). Hydrazine monohydrate (1090 mg, 22 mmol) was slowly added to the mixture at room temperature and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was filtrated, and the filtrate was evaporated under reduced pressure. To the residue were added ethyl acetate and water, and the aqueous layer was extracted with ethyl acetate (×4). Combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate/hexane to give the title compound (1650 mg, 99%) as a pale-yellow solid.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customthe filtrate was evaporated under reduced pressure
  3. additionTo the residue were added ethyl acetate and water
  4. extractionthe aqueous layer was extracted with ethyl acetate (×4)
  5. washCombined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltrated
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. washthe residue was washed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-198229aa597648beb78ec7dbb8d56d2c
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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