Sodium Acetate → (R)-2-Ethyl-6-trifluoromethyl-2,3-dihydro-1H-quinolin-4-one O-methyl-oxime

HRID 661458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661458
CS(O)(=O)=O.[CH2:6]([C@@H:8]1[CH2:17][C@H:16]([NH2:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[NH:9]1)[CH3:7].Cl.[CH3:24][O:25]N.C([O-])(=O)C.[Na+]>O.C1(C)C=CC=CC=1.O1CCCC1>[CH3:24][O:25][N:18]=[C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:19]([F:22])([F:20])[F:21])[CH:14]=2)[NH:9][C@H:8]([CH2:6][CH3:7])[CH2:17]1

Komponenten

7

Edukt 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86636540(2R,4S)-2-Ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinolin-4-ylamine methanesulfonate

Produkt 1

HCID 136390757(R)-2-Ethyl-6-trifluoromethyl-2,3-dihydro-1H-quinolin-4-one O-methyl-oxime

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The compound obtained in Example 2 (2) above (2.43 g), methoxyamine hydrochloride (1.25 g), sodium acetate (1.64 g) and water (2.4 ml) were added to tetrahydrofuran (22 ml) and the mixture was stirred at room temperature for about 48 hours. Toluene (24 ml) and water (12 ml) were added to the reaction mixture, the organic layer was separated, and washed with water (12 ml) and a saturated brine (12 ml). The organic layer was concentrated at reduced pressure and the resulting residue was purified by column chromatography and concentrated to give the titled compound as an oily material (1.92 g, yield 71%). MS (APCI) m/z: 273 [M+H]+.

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with water (12 ml)
  3. concentrationThe organic layer was concentrated at reduced pressure
  4. customthe resulting residue was purified by column chromatography
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-348f6dc224d64718b11e17756e2769de
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084611B2

Notizen zur Reaktion

Wird geladen…