Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isatoic Anhydride | HCID 8359 | — |
| Reactant | Trimethyl orthoformate | HCID 9005 | — |
| Reactant | 3-Bromo-o-toluidine | HCID 123538 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59375063 | HCID 59375063 | 36.2% |
Reaction Steps
A mixture of 1H-benzo[d][1,3]oxazine-2,4-dione (200 mg, 1.226 mmol), 3-bromo-2-methylaniline (228 mg, 1.226 mmol), and trimethoxymethane (390 mg, 3.68 mmol) in THF (2 mL) was heated overnight in a sealed tube at 100° C. The mixture was cooled to room temperature and concentrated, and the residue was purified by column chromatography, eluting with EtOAc-hexane (gradient from 10:90 to 50:50) to provide the desired product (140 mg, 36% yield). LCMS (M+H)+ m/z 315, 317.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08685969B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-c405c12c0fa54e5b9c67a5f59fb7e305 |
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| Source note | uspto-grants-2014_04 |
|---|