P-Anisidine → HCID 178492142, compound

HRID 1985773Notes

Reaction equation

HRID 1985773 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.[S:18]([NH:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)([OH:21])(=[O:20])=[O:19].[OH2:30].C[C:32](C)=[O:33]>>[CH3:9][O:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:5]2[C:4]([NH:22][C:23]3[CH:29]=[CH:28][C:26]([O:33][CH3:32])=[CH:25][CH:24]=3)=[N:3][C:2](=[O:1])[C:7](=[O:8])[CH:6]=2)=[CH:13][CH:12]=1.[S:18]([NH:22][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:5]2[C:4]([NH:27][C:26]3[CH:28]=[CH:29][C:23]([NH:22][S:18]([OH:21])(=[O:19])=[O:20])=[CH:24][CH:25]=3)=[N:3][C:2](=[O:1])[C:7](=[O:8])[CH:6]=2)=[CH:13][CH:12]=1)([OH:20])(=[O:19])=[O:30]

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 10997776p-sulfoaminoanilineHCID 18366337Propan-2-one--water (1/1)HCID 178516237HCID 178516237, compound

Product 2

HCID 178492142HCID 178492142, compoundHCID 178516435HCID 178516435, compound

Procedure

2,3-dihydroxypyridine (0.0021 Mol), p-methoxyaniline (0.0027 mol), p-sulfoaminoaniline (0.0027 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 4 hours, and maintained still overnight. 5-p-methoxyphenylamino-6-(p-sulfoaminophenylamino)-2,3-pyridindione and 6-p-methoxyphenylamino-5-(p-sulfoaminophenylamino)-2,3-pyridindione were purified by passing the filtered reaction mixture through a silica gel column (100-200 mesh). The yield was 12%-16%. 5,6-di(p-methoxyphenylamino)-2,3-pyridindione and 5,6-di(p-sulfoaminophenylamino)-2,3-pyridindione can also be obtained.

Workup

  1. temperaturemaintained still overnight
  2. custom5-p-methoxyphenylamino-6-(p-sulfoaminophenylamino)-2,3-pyridindione and 6-p-methoxyphenylamino-5-(p-sulfoaminophenylamino)-2,3-pyridindione were purified
  3. customthe filtered reaction mixture through a silica gel column (100-200 mesh)

Sources & evidence

ORD record
ord-5cc4ca10819a4ad0a52143bdb44fa761
Source dataset
uspto-grants-2009_06
Patent number
US07547713B2

Reaction notes

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