Sodium Hydroxide → 3-(4-fluorophenyl)-1-(2-methylphenyl)-1H-pyrazol-5-amine

HRID 2109928Notes

Reaction equation

HRID 2109928 reaction equation
N[C:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[CH:3][C:4]#[N:5].Cl.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][NH2:22].[OH-].[Na+]>Cl>[F:12][C:9]1[CH:8]=[CH:7][C:6]([C:2]2[CH:3]=[C:4]([NH2:5])[N:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH3:14])[N:22]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 573643293-Amino-3-(4-fluorophenyl)acrylonitrile

Product 1

HCID 162282833-(4-fluorophenyl)-1-(2-methylphenyl)-1H-pyrazol-5-amineYield 85.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 3-amino-3-(4-fluorophenyl)acrylonitrile (600 mg, 3.70 mmol) in 1 N HCl (6 mL) was added (2-methylphenyl)hydrazine hydrochloride (558 mg, 3.51 mmol). The reaction was allowed to reflux for 16 h, and then cooled to rt. The resulting mixture was basified to pH 12 by slow addition of 1 N aqueous sodium hydroxide. The precipitate was collected by filtration, and then recrystallized from EtOH/Et2O to afford the intermediate (800 mg, 81%) as a light orange solid. 1H NMR (400 MHz, CD2Cl2) δ 2.20 (s, 3H), 2.14 (br s, 2H), 5.91 (s, 1H), 7.06 (t, 2H), 7.36 (d, 4H), 7.75 (m, 2H). This material was used without further purification.

Workup

  1. temperatureto reflux for 16 h
  2. filtrationThe precipitate was collected by filtration
  3. customrecrystallized from EtOH/Et2O

Sources & evidence

ORD record
ord-8853bb84bc754400b54a29d84177cf30
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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