Water → HCID 16953136, compound

HRID 1667832Notes

Reaction equation

HRID 1667832 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[CH3:11][N:12]1[C:16]([C:17](Cl)=[O:18])=[CH:15][C:14]([CH3:20])=[N:13]1.O>CN(C)C(=O)C>[CH3:11][N:12]1[C:16]([C:17]([NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:18])=[CH:15][C:14]([CH3:20])=[N:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 74233-NitroanilineHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chloride

Product 1

HCID 16953136HCID 16953136, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

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. temperaturecooling
  2. filtrationthe mixture was filtrated
  3. washThe obtained solid was washed with water and diethyl ether

Sources & evidence

ORD record
ord-f3dc887eb4434bfd9550f3eb531feded
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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