Pyridine → N-(3-fluorophenyl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide

HRID 639957Notes

Reaction equation

HRID 639957 reaction equation
P(Cl)(Cl)(Cl)=O.[N+:6]([C:9]1[CH:10]=[N:11][N:12]([CH2:14][C:15]([OH:17])=O)[CH:13]=1)([O-:8])=[O:7].[F:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O1CCCC1.O>[F:18][C:19]1[CH:20]=[C:21]([NH:22][C:15](=[O:17])[CH2:14][N:12]2[CH:13]=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=[N:11]2)[CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 97423-FluoroanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 12834772-(4-nitro-1H-pyrazol-1-yl)acetic acid

Product 1

HCID 1504548N-(3-fluorophenyl)-2-(4-nitro-1H-pyrazol-1-yl)acetamideYield 65.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of phosphorus oxychloride (668 mg, 4.40 mmol) in tetrahydrofuran (4 ml) was added to a mixture of (4-nitro-1H-pyrazol-1-yl)acetic acid (684 mg, 4.00 mmol), 3-fluoroaniline (500 mg, 4.5 mmol) and pyridine (1.26 g, 16 mmol) in tetrahydrofuran (20 ml) at 0° C. under argon. The resulting mixture was stirred for 1 hour and an aqueous solution of sodium bicarbonate (20 ml) added. The mixture was further diluted with water and extracted with ethyl acetate (3×50 ml). The organic phase was recovered, dried and concentrated to give an oil which was triturated with diethyl ether:petroleum ether (1:1) to yield N-(3-fluorophenyl)-2-(4-nitro-1H-pyrazol-1-yl)acetamide (695 mg, 65% yield):

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. customThe organic phase was recovered
  3. customdried
  4. concentrationconcentrated
  5. customto give an oil which
  6. customwas triturated with diethyl ether:petroleum ether (1:1)

Sources & evidence

ORD record
ord-9fc90616debd435fb5543bf89a6943b4
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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