Hydrochloric Acid → 5-(3-chloro-4-cyanophenyl)-1H-pyrazole-4-carbonitrile

HRID 872871Notes

Reaction equation

HRID 872871 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:14](C3CCCCO3)[N:13]=[CH:12][C:11]=2[C:21]#[N:22])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[NH:14][N:13]=[CH:12][C:11]=2[C:21]#[N:22])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 671727985-(3-chloro-4-cyanophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 671733195-(3-chloro-4-cyanophenyl)-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution containing 5-(3-chloro-4-cyanophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbonitrile (2.686 g, 8.59 mmol) dissolved in ethanol (25 ml), 10% HCl solution in ethanol (50 ml) was added and the resulting mixture was stirred overnight. The crude product was extracted with DCM/water. The pH of the aqueous phase was adjusted to 12 by adding 2 M NaOH. The aqueous phase was again extracted with DCM. The combined organic phases were dried with Na2SO4, filtered and evaporated. The product was purified by flash chromatography. 1H-NMR (400 MHz; DMSO-d6): δ 8.00-8.05 (m, 1H), 8.13-8.19 (m, 2H), 8.75 (s, 1H), 14.24 (s, 1H).

Workup

  1. extractionThe crude product was extracted with DCM/water
  2. additionby adding 2 M NaOH
  3. extractionThe aqueous phase was again extracted with DCM
  4. dry with materialThe combined organic phases were dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-36b591eaaa84466abae4f8086218ef64
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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