Potassium Hydroxide → HCID 20484902, compound

HRID 647423Notes

Reaction equation

HRID 647423 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([N:12]([C:14]2[CH:27]=[CH:26][C:17]([O:18][CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)[CH3:13])[N:3]=1.[OH-].[K+]>C(O)C.[Pd]>[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([N:12]([C:14]2[CH:27]=[CH:26][C:17]([O:18][CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)[CH3:13])[N:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20484886HCID 20484886, compound

Product 1

HCID 20484902HCID 20484902, compoundYield 14.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 2-{4-[N-(1-chloroisoquinolin-3-yl)-N-methylamino]phenoxy}propionate (2.87 g), in a solution of potassium hydroxide (0.42 g) in ethanol, was hydrogenated at atmospheric pressure over a palladium on carbon catalyst. After uptake of the theoretical amount of hydrogen the solution was filtered to remove the catalyst and the solvent was removed by distillation under reduced pressure. The product was purified by column chromatography over silical gel (eluant dichloromethane/ethylacetate; 99:1) to give ethyl 2-{4-[N-(isoquinolin-3-yl)-N-methylamino]phenoxy}propionate (0.38 g) as a green oil. The assigned structure was confirmed by proton magnetic resonance spectroscopy and mass spectrometry. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.20 (3H, t); 1.60 (3H, d); 3.45 (3H, s); 4.20 (2H, q); 4.70 (1H, q); 6.60 (1H, s); 6.8-7.4 (7H, m); 7.65 (1H, d); 8.90 (1H, s).

Workup

  1. filtrationAfter uptake of the theoretical amount of hydrogen the solution was filtered
  2. customto remove the catalyst
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe product was purified by column chromatography over silical gel (eluant dichloromethane/ethylacetate; 99:1)

Sources & evidence

ORD record
ord-d60d74c0cf0a46f19d97eb206136ce86
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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