HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 1-Chloro-4-methyl-6,7,8,9-tetrahydropyridazino[4,5-b]indolizine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 6,7,8,9-Tetrahydro-4-(methyl)pyridazino[4,5-b]indolizin-1-one | HCID 86752615 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-Chloro-4-methyl-6,7,8,9-tetrahydropyridazino[4,5-b]indolizine | HCID 86752616 | 92% |
Reaction Steps
Compound XI (3.00 g, 15 mmol) was heated under reflux with excess POCl3 (25 mL) until no starting material remained (TLC, silic gel, 5% methanol in methylene chloride), then poured over ice, made basic with aqueous sodium hydroxide and the aqueous phase extracted with methylene chloride to isolate the product. The organic phase was dried (MgSO4), filtered, and evaporated to give a residue which was purified by flash column chromatography (silica gel, 5% methanol in methylene chloride) to give 1-chloro-4-methyl-6,7,8,9-tetrahydropyridazino[4,5-b]indolizine XII (3.00 g, 92%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05756501 |
| Source dataset | uspto-grants-1998_05 |
| ORD ID | ord-c0a2361f749148a4a1e86312db4f23d9 |
| Source note | uspto-grants-1998_05 |