1,3-Dimethyl-2-imidazolidinone → HCID 11492850, compound

Temperature

55 °C

To a 15 ml single neck round-bottom flask equipped with magnetic stirrer and under nitrogen atmosphere was added 60 mg (0.484 mmol) of the sodium salt of methyl 3-hydroxyacrylate in 1.5 ml of DMF. The resulting solution was stirred in the presence of 4A molecular sieves overnight and then filtered into another reaction vessel fitted with condenser, nitrogen line and a magnetic stirrer. To the mixture was charged 52 μl (0.467 mmol) N,N'-dimethylimidazolidinone and the solution was heated to 55° C. To this reactor was added a solution of 93 mg (0.388 mmol) of N-cyclopropyl-6,7-difluoro-2H-3, 1-benzoxazine-2,4(1H) dione in 1.5 ml of DMF. The reaction mixture was stirred at 55° C. for 1 hour. The system was allowed to cool to room temperature and was then added to 30 ml of water at pH 4.0. The pH of the resulting suspension was adjusted to 5.5 and the mixture was cooled to 0° C. and filtered. After drying there was obtained 50 mg (46%) of methyl 1-cyclopropyl-6,7-difluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylate, m.p.: 223° -224° C. The filtrate was extracted with methylene chloride and after drying and evaporation there was obtained an additional 47 mg (43.5%, total yield: 89.5%) of the desired product.

1. customTo a 15 ml single neck round-bottom flask equipped with magnetic stirrer and under nitrogen atmosphere
2. filtrationfiltered into another reaction vessel
3. customfitted with condenser
4. temperatureto cool to room temperature
5. temperaturethe mixture was cooled to 0° C.
6. filtrationfiltered
7. customAfter drying there

ORD record

ord-bb15fb46e3f44f9aa6557848ebde4786

Source dataset

uspto-grants-1991_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05064958