3-Chloroaniline → HCID 178516403, compound

HRID 1985776Notes

Reaction equation

HRID 1985776 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:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13]>O.CC(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([NH:13][C:5]2[C:4]([NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[C:10]([Cl:9])[CH:11]=3)=[N:3][C:2](=[O:1])[C:7](=[O:8])[CH:6]=2)[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 178516237HCID 178516237, compound

Product 1

HCID 178516403HCID 178516403, compoundYield 36%

Reagents, catalysts & solvents 1

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

Procedure

2,3-dihydroxypyridine (0.0027 mol), m-chloroaniline (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(m-chlorophenylamino)-2,3-pyridindione in a yellow powder. The yield was 36%-57%.

Workup

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

Sources & evidence

ORD record
ord-2b2bb8fcf63a4c808f51f544a29adffb
Source dataset
uspto-grants-2009_06
Patent number
US07547713B2

Reaction notes

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