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

HRID 497995Notes

Reaction equation

HRID 497995 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 concentrated under reduced pressure. The residue was poured into water, and organic matter was extracted with a mixture of chloroform/methanol. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue thus obtained 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. concentrationconcentrated under reduced pressure
  3. additionThe residue was poured into water, and organic matter
  4. extractionwas extracted with a mixture of chloroform/methanol
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvents were evaporated under reduced pressure
  8. customThe residue thus obtained
  9. customwas crystallized from ethyl acetate/diethylether/hexane

Sources & evidence

ORD record
ord-d45a2c54da4b4267b3a9c11565638260
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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