Hydrogen Peroxide → HCID 12043647, compound

HRID 2227725Notes

Reaction equation

HRID 2227725 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)=[CH:8][CH:7]=[N:6]1)#[N:2].[OH-:24].[K+].OO>>[F:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:13]2[CH:14]=[CH:15][C:10]([C:9]3[N:5]([CH2:4][CH2:3][C:1]([NH2:2])=[O:24])[N:6]=[CH:7][CH:8]=3)=[CH:11][CH:12]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 22718120HCID 22718120, compound

Product 1

HCID 12043647HCID 12043647, compound

Procedure

Reaction of 3-dimethylamino-1-[4-(4-fluorophenoxy)phenyl]-propenone with 2-cyanoethylhydrazine as described above gave 1-(2-cyanoethyl)-5-[4-(4-fluorophenoxy)phenyl]pyrazole. Reaction of a solution of the nitrile with 10 mL of a 20% aqueous KOH solution and 4 mL of an aqueous 30% H2O2 solution at reflux gave 64 mg of the amide as a white solid, mp 118-120° C. 1H NMR (CDCl3): δ7.54 (d, 1H, J=1.8 Hz), 7.35 (d, 2H, J=8.7 Hz), 7.10-6.98 (m, 6H), 6.26 (d, 1H, J=1.8 Hz), 6.08 (br s, H), 5.30 (br s, 1H), 4.39 (t, 2H, J=6.6 Hz), 2.86 (t, 3H, J=6.6 Hz).

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-be1e15d47b5f4136b15a4b78e7afc2fe
Source dataset
uspto-grants-2002_07
Patent number
US06414011B1

Reaction notes

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