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

HRID 497976Notes

Reaction equation

HRID 497976 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.[NH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[NH2:17]>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:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:17]=1

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 159380972-(2-Oxo-propyl)-benzo[D][1,3]oxazin-4-one

Product 1

HCID 223201402-[[3-Methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acidYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-oxopropyl)-4H-3,1-benzoxazin-4-one (68.2 g, 0.34 mol) and 2-hydrazinopyridine (37.1 g, 0.34 mol) in ethanol (500 mL) was heated under reflux for 1 hour. After the solution was cooled to room temperature, the resulting crystals were collected by filtration. The crystals were washed with ethanol and air dried to give the title compound (50.2 g, 51% yield).

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationthe resulting crystals were collected by filtration
  3. washThe crystals were washed with ethanol and air
  4. customdried

Sources & evidence

ORD record
ord-0973b7eae1204966aadbebc1cb717e81
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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