2-Fluoro-6-methoxybenzonitrile → 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile

HRID 1032907Notes

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

Conditions

Temperature: 60 °C

Procedure

At 50° C. and under a nitrogen blanket, 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 dripped into a solution of 41,2 g (0.273 mol) of 2-methoxy-6-fluorobenzonitrile (preparation: J. Heterocycl. Chem., 25, 1173, 1988) in 50 mi of N, N-dimethylethyleneurea, and the mixture is stirred for 2 hours at 60° C. The batch is cooled and stirred into 4 liters of ice water, and the crystals which precipitate are suction filtered and dried; there is obtained 37.1 g of the product of m.p. 93°-94° C.

Workup

customAt 50° C.
temperatureThe batch is cooled
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-10562c706dbf4e37a5ed2dc40c9cff37
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05308828

Reaction notes

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