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

HRID 915560Notes

Reaction equation

HRID 915560 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 refluxed 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. temperatureThe reaction was refluxed for 16 h
  2. filtrationThe precipitate was collected by filtration
  3. customrecrystallized from EtOH/Et2O

Sources & evidence

ORD record
ord-e3cbf4845e12439ea1cc95c1b857565f
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

Loading…