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

HRID 661458Notes

Reaction equation

HRID 661458 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-348f6dc224d64718b11e17756e2769de
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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