Sodium Acetate → 4-(2-Hydroxyethyl)aminoquinoline

HRID 1646845Notes

Reaction equation

HRID 1646845 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][CH2:14][OH:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+]>[Pd].C(O)(C)C.CO.C(O)(=O)C.O.[OH-].[Na+]>[OH:15][CH2:14][CH2:13][NH:12][C:6]1[C:5]2[C:10](=[CH:11][CH:2]=[CH:3][CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

9

Reactant 2

HCID 517045Sodium AcetateHCID 46504662-[(7-chloroquinolin-4-yl)amino]ethanol

Product 1

HCID 107027774-(2-Hydroxyethyl)aminoquinolineYield 100.6%

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A slurry of 0.86 g of palladium on carbon in isopropanol was pipetted into a Parr shaker and to this was added a solution of 10 g of 7-chloro-N-(2-hydroxyethyl)-4-quinolinamine and 6.1 g of sodium acetate in 260 ml of methanol and 7 ml of acetic acid. The mixture was hydrogenated at 51 psi (pounds per square inch) until no further reaction was observed. Upon filtration through celite and evaporation of solvents an oil resulted which was dissolved in water and basified with sodium hydroxide. A solid resulted which was recrystallized from isopropanol to give 8.5 g of purified compound with a melting point of 152°-154° C.

Workup

  1. customThe mixture was hydrogenated at 51 psi (pounds per square inch) until no further reaction
  2. filtrationUpon filtration
  3. customthrough celite and evaporation of solvents an oil
  4. customresulted which
  5. customA solid resulted which
  6. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-8ce583bbde8040a68a2aded2dea1be38
Source dataset
uspto-grants-1993_01
Patent number
US05182275

Reaction notes

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