Acetone → Ethyl 4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 553541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553541
Cl[C:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.Cl[C:17]1[N:25]=[C:24](C(F)(F)F)C=C[C:18]=1[C:19]([OH:21])=[O:20].C([O-])([O-])=[O:31].[K+].[K+].IC.[CH3:38][C:39](C)=O>>[OH:6][C:4]1[C:3]2[C:2](=[N:11][C:10]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:8]=2)[N:25]([CH3:24])[C:17](=[O:31])[C:18]=1[C:19]([O:21][CH2:38][CH3:39])=[O:20]

Komponenten

6

Edukt 5

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acidHCID 46311111Methyl 2-chloro-6-(trifluoromethyl)pyridine-3-carboxylate

Produkt 1

HCID 57671568Ethyl 4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Versuchsvorschrift

Methyl 2-chloro-6-(trifluoromethyl)nicotinate. To a mixture of 2-chloro-6-(trifluoromethyl)nicotinic acid (available from Fluorochem Products, West Columbia, S.C.) (6.66 g) and K2CO3 (15.7 g, 114 mmol) in acetone (125 mL) was added iodomethane (2.60 mL, 41.7 mmol) dropwise with stirring at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at 35° C. for 18 hours and was then filtered through a plug of Celite®. The filtrate was evaporated under reduced pressure to give the title compound. MS (ESI, pos. ion) m/z: 240 (M+1).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 35° C. for 18 hours
  2. filtrationwas then filtered through a plug of Celite®
  3. customThe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1613789a982d4507b145effdc4114086
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048894B2

Notizen zur Reaktion

Wird geladen…