Iodine → 1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile

HRID 537530Notes

Reaction equation

HRID 537530 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([CH:14]=O)[CH:11]=[N:10]2)=[CH:5][CH:4]=1.II.[OH-].[NH4+:19]>O1CCCC1.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([C:14]#[N:19])[CH:11]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 41239331-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 533021171-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a mixture of 1-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde (80 mg, 0.54 mmol) in tetrahydrofuran (3 mL) and ammonium hydroxide (3 mL) was added iodine (138 mg, 0.54 mmol). The reaction was stirred at room temperature for 5 hours. The reaction was diluted with saturated sodium thiosulphate (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to give 1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile (78 mg, 100%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 8.19 (s, 1H), 7.96 (s, 1H), 7.56 (d, J=9.2 Hz, 2H), 7.01 (d, J=9.2 Hz, 2H), 3.86 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-62e01750ef80407eb6158b93806b1782
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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