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

HRID 1393150Notes

Reaction equation

HRID 1393150 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-bc6f572c8dd84a93bdc3b3ef372354cb
Source dataset
uspto-grants-2008_03
Patent number
US07345064B2

Reaction notes

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