HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (4aR,8aR)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Acetone Cyanohydrin | HCID 6406 | — |
| Reactant | 1,2-Diaminocyclohexane, trans- | HCID 43806 | — |
| Product | (4aR,8aR)-3,3-Dimethyloctahydroquinoxalin-2(1H)-one | HCID 30078391 | — |
Reaction Steps
The disclosure deals with novel synthesis involving (a) hydrogenation of a cis-3,3-dialkyl-3,4-dihydroquinoxaline-2-one in the presence of a suitable hydrogenation catalyst, at elevated temperature and pressure, to yield a cis-3,3-dialkyl decahydroquinoxaline-2-one; (b) reaction of trans-1,2-diaminocyclohexane with acetone cyanohydrin in the presence of water to yield trans-3,3-dimethyl-decahydroquinoxaline-2-one; and (c) a reaction of 1,2-diamine with a saturated acyclic or cyclic monoketone or aldehyde and a holoform, in the presence of (i) a phase transfer catalyst (ii) an organic solvent, and (iii) solid or aqueous alkali to yield 2-keto-1,4-diazacycloalkanes. Such compounds exhibit exceptional UV light stabilizing property.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04711957 |
| Source dataset | uspto-grants-1987_12 |
| ORD ID | ord-d9ef9deefc0843b3822bcbaf9bc53184 |
| Source note | uspto-grants-1987_12 |