Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl formate | HCID 8025 | — |
| Reactant | HCID 22049688 | HCID 22049688 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86760108 | HCID 86760108 | — |
Reaction Steps
4-Methyl-3-[2-(2-methyl-5-nitrophenyl)-1,3-thiazol-4-yl]pyridine (98 mg) and reduced iron (170 mg) were suspended in a mixture of formic acid (3 ml)-ethyl formate (3 ml). 1N Hydrochloric acid (0.2 ml) was added and the mixture was stirred at 80° C. for 12 hrs. The reaction mixture was diluted with ethyl acetate and the insoluble material was filtered off. The organic layer was neutralized with saturated aqueous sodium hydrogen carbonate. The organic layer was separated and concentrated by drying. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=1:1–0:1) for purification. Recrystallization from ethyl acetate gave the title compound (15 mg) as pale-yellow columnar crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07067537B2 |
|---|
| Source dataset | uspto-grants-2006_06 |
|---|
| ORD ID | ord-88631fde30a74d7d84317c3d437802a8 |
|---|
| Source note | uspto-grants-2006_06 |
|---|