N-Methylmorpholine N-oxide monohydrate → HCID 21948859, compound

HRID 2182695Notes

Reaction equation

HRID 2182695 reaction equation
[OH2:1].[CH3:2][N+:3]1([O-])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[N+:10]([C:13]1[CH:22]=[CH:21]C=C2[C:14]=1[CH:15]=[CH:16]C(C=C)=N2)([O-:12])=[O:11]>C(O)(C)C.CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:1][CH:8]([N:3]1[C:4]2[C:14](=[C:13]([N+:10]([O-:12])=[O:11])[CH:22]=[CH:21][CH:5]=2)[CH:15]=[CH:16][CH2:2]1)[CH2:7][OH:6]

Participants

7

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 21948811HCID 21948811, compound

Product 1

HCID 21948859HCID 21948859, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

336 mg (2.5 mmol) of N-methylmorpholine-N-oxide hydrate and 10.22 ml of osmium tetroxide solution in isopropanol are added at 0° C. to a solution that consists of 3.18 g (15.88 mmol) of 5-nitro-2-vinylquinoline in 140 ml of acetone and 21 ml of water, and the reaction mixture is stirred for 24 hours at room temperature. Then, the solvent is removed in a vacuum, and the residue is taken up in ethyl acetate. The organic phase is washed with water and saturated sodium chloride solution. The aqueous phase is extracted repeatedly with dichloromethane, diethyl ether and ethyl acetate. The combined organic phases are dried on sodium sulfate. After removal of the solvent and purification of silica gel with hexane-ethyl acetate (0-100%) as well as with ethyl acetate-methanol (0-20%), 1.64 g (44% of theory) of the product is obtained.

Workup

  1. customThen, the solvent is removed in a vacuum
  2. washThe organic phase is washed with water and saturated sodium chloride solution
  3. extractionThe aqueous phase is extracted repeatedly with dichloromethane, diethyl ether and ethyl acetate
  4. customThe combined organic phases are dried on sodium sulfate
  5. customAfter removal of the solvent and purification of silica gel with hexane-ethyl acetate (0-100%) as well as with ethyl acetate-methanol (0-20%), 1.64 g (44% of theory) of the product
  6. customis obtained

Sources & evidence

ORD record
ord-ce0a04d964694cad9094c952ca23feea
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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