4,4'-Dimethoxybenzil → HCID 13158619, compound

HRID 2205164Notes

Reaction equation

HRID 2205164 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=O)=[CH:5][CH:4]=1.[NH2:21][C:22]1[C:30]([NH2:31])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[N:21][C:22]3[C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=[CH:29][C:30]=3[N:31]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 710434,4'-DimethoxybenzilHCID 1980692,3-Diaminobenzoic acid

Product 1

HCID 13158619HCID 13158619, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1,2-bis(4-methoxyphenyl)ethane-1,2-dione (270 mg, 1.00 mmol, 1.00 equiv) and 2,3-diaminobenzoic acid (152 mg, 1.00 mmol, 1.00 equiv) in acetic acid (10 mL) was heated under reflux for 3 h. The reaction was quenched by the addition of 20 mL of ice/water. The solids were collected by filtration and purified by re-crystallization from methanol, affording 100 mg (26%) of 2,3-bis(4-methoxyphenyl)quinoxaline-5-carboxylic acid as a yellow solid.

Workup

  1. temperatureunder reflux for 3 h
  2. customThe reaction was quenched by the addition of 20 mL of ice/water
  3. filtrationThe solids were collected by filtration
  4. custompurified by re-crystallization from methanol

Sources & evidence

ORD record
ord-87aeb8191a10497fa2f9e77d036a6b4f
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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