Aniline → HCID 178516392, compound

HRID 1985779Notes

Reaction equation

HRID 1985779 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)(=O)C>O.CC(C)=O>[C:10]1([NH:9][C:5]2[C:4]([NH:23][C:22]3[CH:24]=[CH:25][CH:19]=[CH:20][CH:21]=3)=[N:3][C:2](=[O:1])[C:7](=[O:8])[CH:6]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7468p-AminoacetophenoneHCID 178516237HCID 178516237, compound

Product 1

HCID 178516392HCID 178516392, compoundYield 23%

Reagents, catalysts & solvents 1

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

Procedure

2,3-dihydroxypyridine (0.0027 mol), aniline (0.0027 mol), p-acetylaniline (0.0027 mol), and NaIO3 (0.0009 mol) were dissolved in 160 ml water/acetone (80:1, v/v) solvent. The reaction mixture was stirred for 2 hours, and maintained still overnight. The product mixture was filtered, and passed through a silica gel column (200-400 mesh). The final product was 5-p-acetylphenylamino-6-phenylamino-2,3-pyridindione in yellow powder. The yield was 23%-45%. 5,6-diphenylamino-2,3-pyridindione can also be obtained.

Workup

  1. temperaturemaintained still overnight
  2. filtrationThe product mixture was filtered

Sources & evidence

ORD record
ord-0a297e6f138b41d29edbd7e14d45cf54
Source dataset
uspto-grants-2009_06
Patent number
US07547713B2

Reaction notes

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