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

HRID 497938Notes

Reaction equation

HRID 497938 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 crude crystals were filtered. 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 crude crystals were filtered
  3. washThe crystals were washed with ethanol
  4. customair-dried

Sources & evidence

ORD record
ord-8d89519e51e44a01a489ac2a2f2561a8
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

Loading…