Sodium Hydroxide → HCID 86722462, compound

HRID 718848Notes

Reaction equation

HRID 718848 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]#N.[H][H].[OH-:18].[Na+]>[Ni].O.C(O)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[CH:14]=[O:18]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 6886855-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 86722462HCID 86722462, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile (110, R1=4-Fluorophenyl) (56.2 g, 278 mmol), acetic acid (270 mL), water (75 mL) and Raney 2400 Nickel slurry in water (15 g, 278 mmol) was shaken under about 30 psi hydrogen at about 20°-25° C. for about 8 h. The mixture was filtered through a pad of Celite®. The contents of the reaction vessel were transferred with acetic acid (150 mL) and the pad was washed with an additional portion of acetic acid (200 mL). The filtrate was concentrated under reduced pressure to give a slurry. Water (300 mL) was added then the mixture was stirred for about 15 min. The mixture was cooled in an ice/water bath then basified with 5 N aq. NaOH. After stirring for about 20 min in the ice/water bath the solids were collected by filtration and washed with water (100 mL).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washthe pad was washed with an additional portion of acetic acid (200 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a slurry
  5. temperatureThe mixture was cooled in an ice/water bath
  6. filtrationwere collected by filtration
  7. washwashed with water (100 mL)

Sources & evidence

ORD record
ord-cd85ba35108747639e0526606092fb65
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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