4,4'-Dimethoxybenzil → 2,3-Bis(4-methoxyphenyl)quinoxaline-6-carbonitrile

HRID 1405494Notes

Reaction equation

HRID 1405494 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[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[NH2:30])[C:25]#[N:26]>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:29](=[CH:28][CH:27]=[C:24]([C:25]#[N:26])[CH:23]=3)[N:30]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 710434,4'-DimethoxybenzilHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 670419752,3-Bis(4-methoxyphenyl)quinoxaline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of 1,2-bis(4-methoxyphenyl)ethane-1,2-dione (200 mg, 0.74 mmol, 1.00 equiv) in acetic acid (20 mL), 3,4-diaminobenzonitrile (118.2 mg, 0.89 mmol, 1.20 equiv). The resulting solution was stirred for 1 h at reflux in an oil bath. The reaction was then quenched by the addition of water. The solids were collected by filtration and washed with MeOH. This resulted in 205 mg (71%) of 2,3-bis(4-methoxyphenyl)quinoxaline-6-carbonitrile as a yellow solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. temperatureat reflux in an oil bath
  3. customThe reaction was then quenched by the addition of water
  4. filtrationThe solids were collected by filtration
  5. washwashed with MeOH
  6. customThis resulted in 205 mg (71%) of 2,3-bis(4-methoxyphenyl)quinoxaline-6-carbonitrile as a yellow solid

Sources & evidence

ORD record
ord-3bfb3bb366d84ee2a721a7467eb2b7b5
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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