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

HRID 2205163Notes

Reaction equation

HRID 2205163 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=O)[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=O)=[CH:15][CH:14]=1>C(O)(=O)C>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:20]2[C:19]([C:16]3[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=3)=[N:1][C:2]3[C:9](=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=3)[N:10]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

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

Product 1

HCID 670419752,3-Bis(4-methoxyphenyl)quinoxaline-6-carbonitrileYield 72.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,4-diaminobenzonitrile (50 mg, 0.30 mmol, 1.00 equiv, 80%) and 1,2-bis(4-methoxyphenyl)ethane-1,2-dione (89 mg, 0.33 mmol, 1.00 equiv) in acetic acid (5 mL) was stirred for 30 min at 30° C. in an oil bath, then at 130° C. for 3 h. The reaction was quenched with 10 mL of water. The solids were collected by filtration and dried in an oven under reduced pressure, yielding 80 mg (72%) of 2,3-bis(4-methoxyphenyl)quinoxaline-6-carbonitrile as a yellow solid.

Workup

  1. customThe reaction was quenched with 10 mL of water
  2. filtrationThe solids were collected by filtration
  3. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-c522b36d2a2240f6acbb5b51ac090212
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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