Potassium Carbonate → 2-(Trifluoromethyl)quinolin-5-amine

HRID 2054971Notes

Reaction equation

HRID 2054971 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]([C:14]([F:17])([F:16])[F:15])=[N:9]2)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([C:14]([F:17])([F:15])[F:16])=[N:9]2

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 219488215-Nitro-2-(trifluoromethyl)quinoline

Product 1

HCID 219487892-(Trifluoromethyl)quinolin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

390 mg (1.61 mmol) of 5-nitro-2-(trifluoromethyl)quinoline is dissolved in 13 ml of methanol. After the addition of 39 mg of palladium on carbon and 19 mg of potassium carbonate, 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%), 250 mg (73% 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%), 250 mg (73% of theory) of the product is obtained

Sources & evidence

ORD record
ord-3d723170792f43d4abd3f8d591563c31
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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