Acetic Acid → 4-Phenyl-2-pyridin-2-yl-2H-pyrazol-3-ylamine

HRID 645476

Reaction equation

HRID 645476 reaction equation
O[CH:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5].CC(O)=O.[NH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[NH2:17]>CCO>[C:6]1([C:3]2[CH:2]=[N:17][N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:4]=2[NH2:5])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 786452-HydrazinopyridineHCID 907593-Hydroxy-2-phenylacrylonitrile

Product 1

HCID 687067094-Phenyl-2-pyridin-2-yl-2H-pyrazol-3-ylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-hydroxy-2-phenylacrylonitrile (3.4 mmol) in EtOH (6.8 mL) is added AcOH (0.66 mL) and 2-hydrazinopyridine (6.8 mmol) at room temperature. After stirred at 80° C. for 5 h, the reaction mixture is cooling and concentrated in vacuo. The residue is diluted with H2O and extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue is triturated with ether to give the title compound; 1H NMR (CDCl3) δ 6.27 (br, 2H), 7.11-7.14 (m, 1H), 7.21-7.25 (m, 1H), 7.40-7.48 (m, 4H), 7.65 (s, 1H), 7.79-7.84 (m, 1H), 8.02 (d, 1H), 8.35-8.37 (m, 1H).

Workup

  1. temperaturethe reaction mixture is cooling
  2. concentrationconcentrated in vacuo
  3. additionThe residue is diluted with H2O
  4. extractionextracted with AcOEt
  5. washThe organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue is triturated with ether

Sources & evidence

ORD record
ord-bc906fac262d4b8783bd1767fc1239b3
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Linked notes

Loading…