HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 6-(4-Hydroxy-3-methoxy-phenyl)-2-(4-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | Toluene-4-sulfonic acid 2-methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-phenyl ester | HCID 57649518 | — |
| Solvent | Water | HCID 962 | — |
| Product | 6-(4-Hydroxy-3-methoxy-phenyl)-2-(4-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one | HCID 68950959 | 88.2% |
Reaction Steps
Combine toluene-4-sulfonic acid 2-methoxy-4-[2-(4-methoxy-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-phenyl ester (1.029 g, 1.92 mmol) and KOH (2.15 g, 38.48 mmol) with EtOH (30 mL) and water (20 mL). Reflux the reaction for 10 h and dilute with water (50 mL). Acidify with 5.0 M HCl (8 mL). Remove the organic solvent in vacuo and dilute the residue with water (10 mL). Collect the solid material by filtration and wash with water (3×10 mL) and Et2O (2×15 mL) then dry in a vacuum oven to give 0.646 g (88%) of the title compound. MS/ES m/z 382.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08263772B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-e3bf5dfec2714364aead372e5df1478e |
| Source note | uspto-grants-2012_09 |