HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Methyl-3-oxo-2,3,5,6,8,9-hexahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | HCID 6775 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Methyl-3-oxo-2,3,4,4a,5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester | HCID 86686058 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-Methyl-3-oxo-2,3,5,6,8,9-hexahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester | HCID 86686059 | 52.4% |
Reaction Steps
3 g DDQ was added to 2.5 g 2-methyl-3-oxo-2,3,4,4a,5,6,8,9-octahydro-1,2,7-triaza-benzocycloheptene-7-carboxylic acid tert-butyl ester in 25 mL dioxane. The reaction was refluxed for 12 h. Then aqueous potassium carbonate solution was added and the mixture was extracted with chloroform. The organic layer was washed with brine. The crude product was purified by column chromatography on silica gel to yield 1.3 g of the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08741892B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-3d7c3baae2f74170bb803737c9f5c040 |
| Source note | uspto-grants-2014_06 |