O-Toluidine → HCID 178424344, compound

HRID 1985777Notes

Reaction equation

HRID 1985777 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12]>O.CC(C)=O>[C:10]1([CH3:9])[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][C:5]1[C:4]([NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH3:9])=[N:3][C:2](=[O:1])[C:7](=[O:8])[CH:6]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 178516237HCID 178516237, compound

Product 1

HCID 178424344HCID 178424344, compoundYield 27%

Reagents, catalysts & solvents 1

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

Procedure

2,3-dihydroxypyridine (0.0027 mol), o-methylaniline (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(o-tolylamino)-2,3-pyridindione in a red powder. The yield was 27%-45%.

Workup

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

Sources & evidence

ORD record
ord-52b10663f111446ab8a3acc934e8d510
Source dataset
uspto-grants-2009_06
Patent number
US07547713B2

Reaction notes

Loading…