Pyrazole → 1-(3-nitrophenyl)-1H-pyrazole

HRID 581946Notes

Reaction equation

HRID 581946 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[NH:11]1[CH:15]=[CH:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[N+:8]([C:4]1[CH:3]=[C:2]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 125741-Iodo-3-nitrobenzene

Product 1

HCID 121007811-(3-nitrophenyl)-1H-pyrazoleYield 96%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1-iodo-3-nitrobenzene (18.7 g, 75 mmol), pyrazol (7.66 g, 113 mmol), potassium carbonate (11.2 g, 81 mmol) and catalytic amounts of cuprous iodide and copper-bronze in dry N-methyl-2-pyrrolidone (50 ml) is heated to 180° C. for 4.5 hours. After cooling the mixture is filtered through celite. The filtrate is poured into ice water (700 ml) and the product is filtered off, washed with water and dried to yield 13.57 g. Yield: 96%. Mp 85-87° C.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationis filtered through celite
  3. additionThe filtrate is poured into ice water (700 ml)
  4. filtrationthe product is filtered off
  5. washwashed with water
  6. customdried
  7. customto yield 13.57 g

Sources & evidence

ORD record
ord-54e41fdecb8e4021b5ecfe8c075c7e9d
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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