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

HRID 2075881Notes

Reaction equation

HRID 2075881 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

A catalytic amount of 10% palladium on carbon was added to a solution of 3-(4-quinolyl)-2-propenylamine (Intermediate No. 2-4) (188 mg, 1.02 mmol) obtained in Preparation Example 2 in methanol (3 ml) at room temperature under a nitrogen atmosphere, 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 resulting residue was distributed with 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 145 mg (76.3%) of the titled compound.

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-d394dfcdfdfa4a5094f44f043d042c96
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Reaction notes

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