HCID 136375547, compound → HCID 19387893, compound

HRID 1757444Notes

Reaction equation

HRID 1757444 reaction equation
[C:1](=[N:14]O)([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:2][CH3:3]>[Pd].C(O)(=O)C>[NH2:14][CH:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 136375547HCID 136375547, compound

Product 1

HCID 19387893HCID 19387893, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Example P-11: 4.0 g of 2-propionylquinoline-oxime and 2 g of 5 % Pd/C catalyst in 40 ml of glacial acetic acid are placed in a hydrogenation apparatus. The batch is hydrogenated for 5 hours at 20°-25° C. under normal pressure. Filtration is then carried out, the glacial acetic acid is removed under a water-jet vacuum and the residue is purified by means of flash chromatography on silica gel (eluant: ethanol/ether 1:1 ) to yield 3.6 g of 2-(1-aminopropyl)quinoline in the form of a red oil (1H-NMR).

Workup

  1. filtrationFiltration
  2. customthe glacial acetic acid is removed under a water-jet vacuum
  3. customthe residue is purified by means of flash chromatography on silica gel (eluant: ethanol/ether 1:1 )

Sources & evidence

ORD record
ord-c789f8c7cf494d6b81578b2ed4d17fc7
Source dataset
uspto-grants-1995_08
Patent number
US05446040

Reaction notes

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