Sodium Acetate → 2-[[3-Methyl-1-(3-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid

HRID 497945Notes

Reaction equation

HRID 497945 reaction equation
O=[C:2]([CH3:15])[CH2:3][C:4]1[O:9][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]=1.Cl.Cl.[NH:18]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[NH2:19].C([O-])(=O)C.[Na+]>C(O)C>[CH3:15][C:2]1[CH:3]=[C:4]([NH:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:9])=[O:10])[N:18]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:19]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 159380972-(2-Oxo-propyl)-benzo[D][1,3]oxazin-4-oneHCID 171324893-Hydrazinylpyridine dihydrochloride

Product 1

HCID 223201942-[[3-Methyl-1-(3-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acidYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-oxopropyl)-4H-3,1-benzoxazin-4-one (10.2 g, 50.0 mmol), 3-hydrazinopyridine dihydrochloride (9.10 g, 50.0 mmol) and sodium acetate (9.84 g, 120 mmol) in ethanol (100 mL) was heated under reflux for 1 hour. The solution was cooled to room temperature, and the reaction solvent was evaporated under reduced pressure. The residue was poured into water, and organic matter was extracted with a mixed solvent of chloroform/methanol. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was crystallized from ethyl acetate/diethylether/hexane to give the title compound (10.1 g, 69% yield).

Workup

  1. temperatureunder reflux for 1 hour
  2. customthe reaction solvent was evaporated under reduced pressure
  3. additionThe residue was poured into water, and organic matter
  4. extractionwas extracted with a mixed solvent of chloroform/methanol
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate/diethylether/hexane

Sources & evidence

ORD record
ord-6e4c35ce488f4fd8825b7cff7fded5e8
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

Loading…