Toluene → HCID 178469351, Verbindung

To a mixture of diethyl oxalacetate sodium salt (10.5 g, 50 mmol), acetic acid (100 mL) and toluene (50 mL) was added an aqueous solution (50 mL) of (2-methylphenyl)hydrazine hydrochloride (7.93 g, 50 mmol) under stirring at room temperature, and the mixture was heated under reflux for 3 hr. After cooling, the reaction mixture was partitioned. The organic layer was washed with water and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-3/1) to give yellow crystals. This product was dissolved in acetic acid (36 mL), and the mixture was heated under reflux for 2 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and recrystallized from hexane-ethyl acetate to give the title compound (2.69 g, yield 22%) as colorless crystals.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 3 hr
3. temperatureAfter cooling
4. customthe reaction mixture was partitioned
5. washThe organic layer was washed with water and saturated brine
6. customdried
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-3/1)
9. customto give yellow crystals
10. temperaturethe mixture was heated
11. temperatureunder reflux for 2 hr
12. temperatureAfter cooling
13. concentrationthe reaction mixture was concentrated under reduced pressure
14. customrecrystallized from hexane-ethyl acetate

ORD-Eintrag

ord-fe755205ce944513b949e8d98f2dc66a

Quelldatensatz

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07786165B2