2-Fluoro-6-methoxybenzonitrile → 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
Reaction equation
[N-:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[Na+].[CH3:7][O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13](F)[C:10]=1[C:11]#[N:12]>CN(C(N1CC1)=O)C>[CH3:7][O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[C:10]=1[C:11]#[N:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 0.273 mol of sodium pyrazolide (prepared from equimolar amounts of pyrazole and sodium hydride) in 140 ml of N,N-dimethylethyleneurea is added dropwise at 50° C., under nitrogen, to a solution of 41.2 g (0.273 mol) of 2-methoxy-6-fluorobenzonitrile (preparation: J. Heterocycl. Chem. 25 (1988), 1173) in 50 ml N,N-dimethylethyleneurea and the mixture is stirred at 60° C. for 2h. After the mixture has been cooled and stirred into 4 l of ice water and the precipitated crystals have been filtered off under suction and dried, 37.1 g of the product of melting point 93°-94° C. are obtained.
Workup
- temperatureAfter the mixture has been cooled
- filtrationthe precipitated crystals have been filtered off under suction
- customdried
Sources & evidence
- ORD record
- ord-de2e4e27d32a40c584ca8c1a6eba9c3b
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05085686
Reaction notes
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