4-Chloroaniline → HCID 178516413, compound

HRID 1985774Notes

Reaction equation

HRID 1985774 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1>O.CC(C)=O>[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([NH:14][C:5]2[C:4]([NH:14][C:13]3[CH:15]=[CH:16][C:10]([Cl:9])=[CH:11][CH:12]=3)=[N:3][C:2](=[O:1])[C:7](=[O:8])[CH:6]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 178516237HCID 178516237, compound

Product 1

HCID 178516413HCID 178516413, compoundYield 42%

Reagents, catalysts & solvents 1

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

Procedure

2,3-dihydroxypyridine (0.0027 mol), p-chloroaniline (0.0054 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. It was then filtered and recrystallized with chloroform. The final product was 5,6-di(p-chlorophenylamino)-2,3-pyridindione in a yellow powder. The yield was 42%-60%.

Workup

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

Sources & evidence

ORD record
ord-103a8030125e4e468dc66cd7e426a0a3
Source dataset
uspto-grants-2009_06
Patent number
US07547713B2

Reaction notes

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