HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hexane → 3-(4-bromo-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 2-[2-(4-Bromo-phenyl)-propionylamino]-4,6-dichlorobenzoic acid methyl ester | HCID 68816564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(4-bromo-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione | HCID 11560362 | 18% |
Reaction Steps
The objective compound was prepared by the same procedure for the example 1, using a 2-[2-(4-bromo-phenyl)-propionyl amino]-4,6-dichloro-benzoic acid methyl ester (400 mg, 0.93 mmol) and NaH (78 mg, 1.95 mmol) as a base instead of LiHMDS. After normal workup, the objective compound (60 mg, 18%) was obtained as white solid by a flash column chromatography (n-hexane:EtOAc=5:1): 1H NMR (200 MHz, CDCl3+CD3OD) δ 1.69 (s, 3H, CH3), 6.91-7.48 (m , 6H, ArH); m.p. 237-238° C.; MS(EI) m/e 397 [M+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07592457B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-8ee734c2109340dda1f22ffd2c677d28 |
| Source note | uspto-grants-2009_09 |