Potassium Carbonate → 5-Amino-2-(morpholin-4-ylmethyl)quinoline

HRID 2055006Notes

Reaction equation

HRID 2055006 reaction equation
[N:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[N+:18]([O-])=O)[N:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO.[Pd]>[NH2:18][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[CH:17][C:8]([CH2:7][N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1)=[N:9]2

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 219488002-(Morpholin-4-ylmethyl)-5-nitroquinoline

Product 1

HCID 219488345-Amino-2-(morpholin-4-ylmethyl)quinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

190 mg (0.7 mmol) of 2-(morpholin-4-ylmethyl)-5-nitroquinoline is dissolved in 10 ml of methanol. After the addition of 19 mg of palladium on carbon and 19 mg of potassium carbonate, the reaction mixture is allowed to stir for 4 hours at room temperature under hydrogen atmosphere. It is then filtered on Celite and washed with ethyl acetate. After removal of the solvent in a vacuum and chromatography on silica gel with hexane-ethyl acetate (0-100%) as well as with ethyl acetate-methanol (0-100%), 134 mg (79% of theory) of the product is obtained.

Workup

  1. filtrationIt is then filtered on Celite
  2. washwashed with ethyl acetate
  3. customAfter removal of the solvent in a vacuum and chromatography on silica gel with hexane-ethyl acetate (0-100%) as well as with ethyl acetate-methanol (0-100%), 134 mg (79% of theory) of the product
  4. customis obtained

Sources & evidence

ORD record
ord-d8af3d6575ac44c2881f5fbe604cc5f9
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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