Sodium Acetate → 2-[[3-Methyl-1-(4-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid

HRID 497997

Reaction equation

HRID 497997 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.[NH:17]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[NH2:18].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:17]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[N:18]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 159380972-(2-Oxo-propyl)-benzo[D][1,3]oxazin-4-oneHCID 223202584-Hydrazinylpyridine hydrochloride

Product 1

HCID 223202272-[[3-Methyl-1-(4-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acidYield 49.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-oxopropyl)-4H-3,1-benzoxazin-4-one (16.7 g, 82.4 mmol), 4-hydrazinopyridine hydrochloride (12.0 g, 82.4 mmol) and sodium acetate (8.10 g, 98.9 mmol) in ethanol (300 mL) was heated under reflux for 30 minutes. The solution was cooled to room temperature and concentrated under reduced pressure. The residue was poured into water and the resulting crude crystals were collected by filtration. The crystals were washed with ethanol and air dried to give the title compound (11.9 g, 49% yield).

Workup

  1. temperatureunder reflux for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was poured into water
  4. filtrationthe resulting crude crystals were collected by filtration
  5. washThe crystals were washed with ethanol and air
  6. customdried

Sources & evidence

ORD record
ord-59f508b342ef4dfb8bbe3d56c92b80dc
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Linked notes

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