P-Anisidine → HCID 178492142, compound

HRID 1985775Notes

Reaction equation

HRID 1985775 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>O.CC(C)=O>[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:5]2[C:4]([NH:15][C:14]3[CH:16]=[CH:17][C:11]([O:10][CH3:9])=[CH:12][CH:13]=3)=[N:3][C:2](=[O:1])[C:7](=[O:8])[CH:6]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 178516237HCID 178516237, compound

Product 1

HCID 178492142HCID 178492142, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

2,3-dihydroxypyridine (0.0027 mol), p-methoxyaniline (0.0054 mol); and NaIO3 (0.0009 mol) were dissolved in 160 ml of water/acetone (80:1, v/v) solvent. The reaction mixture was stirred for 2 hours, and maintained still overnight. It was then filtered, and recrystallized with chloroform. The final product was 5,6-di(p-methoxyphenylamino)-2,3-pyridindione in a red powder. The yield was 32%-50%.

Workup

  1. temperaturemaintained still overnight
  2. filtrationIt was then filtered
  3. customrecrystallized with chloroform

Sources & evidence

ORD record
ord-5bfc5170b7b249ba9d521dab933c6976
Source dataset
uspto-grants-2009_06
Patent number
US07547713B2

Reaction notes

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