Sodium Chloride → 1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carbonitrile

HRID 475500Notes

Reaction equation

[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]([NH2:11])=O)=[N:2]1.[Cl-].[Na+].P(Cl)(Cl)(Cl)=O>C(#N)C>[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3]([C:9]#[N:11])=[N:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

1,4,5,6-Tetrahydro-cyclopentapyrazole-3-carboxylic acid amide (0.210 g, 1.39 mmol) was added to anhydrous acetonitrile (12 cm3), heated to 80° C. and sodium chloride (2.0 g, 34-mmol) added. After 15 minutes phosphorus oxychloride (0.128 g, 0.83 mmol) was added and the solution heated to 80° C. overnight, cooled, filtered, and the collected solid washed with acetonitrile. Solvent was removed from the combined solutions under reduced pressure and the resulting solid purified by preparative HPLC to give 1,4,5,6-tetrahydro-cyclopentapyrazole-3-carbonitrile as a deep purple coloured solid (0.031 g, 0.23 mmol, 17%). δH (CD3OD): 2.79 (t like, 2H, J=7.3), 2.73 (t like, 2H, J=7.1), 2.65-2.55 (m, 2H); m/z (ES+): 134 [M+H]+.

Workup

temperaturethe solution heated to 80° C. overnight
temperaturecooled
filtrationfiltered
washthe collected solid washed with acetonitrile
customSolvent was removed from the combined solutions under reduced pressure
customthe resulting solid purified by preparative HPLC

Sources & evidence

ORD record: ord-b715a3541ca34ee298e9497ac23a7e2f
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637555B2

Reaction notes

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