Sodium Carbonate → HCID 21948806, compound

HRID 2182682Notes

Reaction equation

HRID 2182682 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH:14]=[CH2:15])=[N:9]2)([O-])=O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.[Pd]>[CH2:14]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[NH2:1])[N:9]=1)[CH3:15]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 21948811HCID 21948811, compound

Product 1

HCID 21948806HCID 21948806, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g (5.0 mmol) of 5-nitro-2-vinylquinoline is dissolved in 30 ml of ethyl acetate. After 100 mg of palladium on carbon and 50 mg of sodium carbonate are added, the reaction mixture is allowed to stir for 20 hours at room temperature under hydrogen atmosphere. It is then filtered on Celite and washed with ethyl acetate. After the solvent is removed in a vacuum and after chromatography on silica gel with hexane-ethyl acetate (0-100%), then with ethyl acetate-methanol (0-30%), 720 mg (84% of theory) of the product is obtained.

Workup

  1. filtrationIt is then filtered on Celite
  2. washwashed with ethyl acetate
  3. customAfter the solvent is removed in a vacuum
  4. customafter chromatography on silica gel with hexane-ethyl acetate (0-100%), then with ethyl acetate-methanol (0-30%), 720 mg (84% of theory) of the product is obtained

Sources & evidence

ORD record
ord-b96ad7346bec450087d3a2b156035681
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

Loading…