3-(4-Quinolyl)-2-propenylamine → 3-(Quinolin-4-yl)propan-1-amine

HRID 18389Notes

Reaction equation

HRID 18389 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[CH:12][CH2:13][NH2:14])=[CH:3][CH:2]=1>[Pd].CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][CH2:13][NH2:14])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 671188043-(4-Quinolyl)-2-propenylamine

Product 1

HCID 121366393-(Quinolin-4-yl)propan-1-amineYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, 10% palladium on carbon (catalytic amount) was added to a solution of 3-(4-quinolyl)-2-propenylamine (Intermediate No. 2-4) (188 mg, 1.02 mmol) in methanol (3 ml) at room temperature, and the mixture was stirred under a hydrogen atmosphere overnight. The reaction mixture was filtered with Celite, the solvent was evaporated under reduced pressure, and the obtained residue was distributed between ethyl acetate (30 ml) and a saturated aqueous ammonium chloride solution (30 ml). A 4 N aqueous sodium hydroxide solution (30 ml) was added to the aqueous layer, the whole was extracted with chloroform (100 ml), and the obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the target compound (145 mg, 76.3%).

Workup

  1. filtrationThe reaction mixture was filtered with Celite
  2. customthe solvent was evaporated under reduced pressure
  3. additionA 4 N aqueous sodium hydroxide solution (30 ml) was added to the aqueous layer
  4. extractionthe whole was extracted with chloroform (100 ml)
  5. dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-dc0456fbc17541e3b51d262d4e41a565
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Reaction notes

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