Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Glyoxal | HCID 7860 | — |
| Reactant | 3,5-Diamino-2-methylbenzoic acid | HCID 135524 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | Methyl 6-quinoxalinecarboxylate | HCID 2781239 | 93% |
Reaction Steps
To a stirred solution of 3,4-diamino-benzoic acid methyl ester (236, 2 g, 12.03 mmol) in isopropanol (50 mL) was added oxaldehyde as a 40% solution in water (13.23 mmol, 1.52 mL). The reaction mixture was heated at 80° C. for 2 hours, the solvent was removed under reduced pressure and the residue was dried under vacuum to yield 237a as a yellow solid (2.09 g, 93% yield). 1H NMR: (DMSO) δ 9.01 (s, 2H), 8.54 (d, J=1.6 Hz, 1H), 8.23 (dd, J=8.6, 2.0 Hz, 1H), 8.14 (dd, J=8.6, 0.6 Hz, 1H), 3.35 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07868205B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-92196afd2d9848e78673ee2addf86140 |
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| Source note | uspto-grants-2011_01 |
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