P-Anisidine → HCID 2944858, compound

HRID 1394171Notes

Reaction equation

HRID 1394171 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 517045Sodium AcetateHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 2944858HCID 2944858, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-chloro-3-nitropyridine (Kruger J, Mann F. G, J. Chem. Soc., 1955, 2755) (700 mg, 4.41 mmol) in ethanol (10 ml) was added 4-methoxyaniline (1.087 g, 8.82 mmol), followed by sodium acetate (362 mg, 4.41 mmol). The mixture was heated under reflux for 16 hours, cooled to room temperature and diluted with water (30 ml). The resulting precipitate was collected by filtration, washed with water (×3) and dried in vacuo to afford the title compound (800 mg, 74%); MS (ES+) m/e 309 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water (×3)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-75a91a17c6a548418d72f27e4b633f8f
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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