Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glyoxal | HCID 7860 | — |
| Reactant | 3-Nitro-1,2-phenylenediamine | HCID 4359525 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | Quinoxaline, 5-nitro- | HCID 97512 | 97.5% |
Reaction Steps
Oxaldehyde (40% in water; 1.43 ml, 31.3 mmol) was added to a solution of 3-nitro-o-phenylene-diamine (600 mg, 3.9 mmol) in EtOH (15 ml) and the mixture was heated at 85° C. for 2 h. The solvent was removed in vacuo, the residue was diluted in water and the aqueous phase was extracted with DCM. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (99:1) as the eluent to give the title compound (666 mg, 97%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09102688B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-aa1fa3bc74884eecb8bf344e5a373036 |
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| Source note | uspto-grants-2015_08 |
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