HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 397493Generated: October 26, 2026
Ethyl orthoformate → Ethyl acetate methanol ammonium hydroxide
https://huagongshe.com/reaction/397493
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl orthoformate | HCID 31214 | — |
| Reactant | Methyl 5,6-diaminopyridine-3-carboxylate | HCID 9920476 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Product | Ethyl acetate methanol ammonium hydroxide | HCID 21901312 | — |
| Product | Methyl 1h-imidazo[4,5-b]pyridine-6-carboxylate | HCID 71433321 | — |
Reaction Steps
A mixture of methyl-5,6-diaminonicotinate (461 mg, 2.76 mmol), formic acid (250 μL) and triethyl orthoformate (7.5 mL) was heated to 100° C. for 2 h. The mixture was then concentrated to an oily solid. Silica gel chromatography (8:1:1 EtOAc-MeOH—NH4OH) afforded the title compound as a cream-colored solid: Rf (8:1:1 EtOAc-MeOH—NH4OH)=0.22; 1H NMR (400 MHz, DMSO-d6): δ8.94 (d, J=2.0 Hz, 1H), 8.64 (s, 1H), 8.50 (d, J=2.0 Hz, 1H), 3.91 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06610701B2 |
|---|
| Source dataset | uspto-grants-2003_08 |
|---|
| ORD ID | ord-6c3abf7ed18846c09fa666755f45f827 |
|---|
| Source note | uspto-grants-2003_08 |
|---|
