6-(3-Azidopropoxy)carbostyril → 6-(3-Aminopropoxy)carbostyril

HRID 1856749Notes

Reaction equation

HRID 1856749 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]2)=[N+]=[N-]>C(OCC)(=O)C.CO.[C].[Pd]>[NH2:1][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]2

Participants

4

Reactant 1

HCID 221326056-(3-Azidopropoxy)carbostyril

Product 1

HCID 100136326-(3-Aminopropoxy)carbostyrilYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 6-(3-azidopropoxy)carbostyril (17.5 g) in a mixture of ethyl acetate-methanol (1:1, 700 ml) is added 10% palladium-carbon (1.75 g), and the mixture is subjected to hydrogenation at room temperature under atmospheric pressure. After the reaction is complete, the catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure to remove the solvent. The resulting residue is washed with diethyl ether to give 6-(3-aminopropoxy)carbostyril (14.7 g) as a white powder.

Workup

  1. customis subjected to hydrogenation at room temperature under atmospheric pressure
  2. customthe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customto remove the solvent
  5. washThe resulting residue is washed with diethyl ether

Sources & evidence

ORD record
ord-1b76b7212cce43dea9e620481a64bd41
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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