HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 2H-1,2-Benzoxazin-3(4H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 4-Chloroaniline | HCID 7812 | — |
| Reactant | Trimethylacetamide | HCID 12957 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | 2H-1,2-Benzoxazin-3(4H)-one | HCID 19937448 | — |
Reaction Steps
This general method teaches (1) metallation of the pivalamide of parachloroaniline with n-butyllithium followed by nucleophilic substitution with an ester to form a ketone, (2) synthesis of a tertiary carbinol by Grignard addition to the ketone, and (3) cyclization of the unprotected amine with the carbinol by addition of a condensing agent to form a benzoxazinone.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06348616B1 |
| Source dataset | uspto-grants-2002_02 |
| ORD ID | ord-30e89d7f2e944a8fb5ce9258d2a39fa1 |
| Source note | uspto-grants-2002_02 |