HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl 8-cyano-2-naphthoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | HCID 6775 | — |
| Reactant | Methyl 8-cyano-5,6-dihydro-2-naphthoate | HCID 14756558 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Methyl 8-cyano-2-naphthoate | HCID 14756562 | — |
Reaction Steps
The remaining naphthoate (11) was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in dioxane to aromatize the adjacent ring to give the methyl 8-cyano-2-naphthoate (13). Then, the nitrile was reduced via hydrogentation and the methyl ester saponified to the carboxylic acid. This acid was then N-BOC-protected to give N-(BOC)-8-aminomethyl-2-naphthoic acid (14) as an intermediate for incorporation into the cyclic peptide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05879657 |
| Source dataset | uspto-grants-1999_03 |
| ORD ID | ord-1d7c7a5f523844a4b75b3db5a0a5c43a |
| Source note | uspto-grants-1999_03 |