Hydrogen Bromide → HCID 15590492, compound

HRID 1730910Notes

Reaction equation

HRID 1730910 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH:7]([CH2:22][CH3:23])[C:8]([C:10]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]3[C:11]=2[CH2:12][CH2:13][C:14](=[O:21])[NH:15]3)=[O:9])[CH2:3][CH2:2]1.Br.[H][H]>O.[Pd]>[O:1]1[CH2:6][CH2:5][N:4]([CH:7]([CH2:22][CH3:23])[CH:8]([C:10]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]3[C:11]=2[CH2:12][CH2:13][C:14](=[O:21])[NH:15]3)[OH:9])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 13199847HCID 13199847, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15590492HCID 15590492, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 962WaterSolvent

Procedure

1.0 g of 5-(2-morpholinobutyryl)-8-hydroxy-3,4-dihydrocarbostyril (IIb) hydrobromide was dissolved in 70 ml of water and 0.2 g of palladium-on-carbon and 0.3 g of palladium black were added to the solution followed by allowing the mixture to catalytically reduce under atmospheric pressure in a hydrogen atmosphere for 10 days at a temperature of 70° C while shaking. After completion of the reduction, the reaction mixture was filtered to remove the catalysts by filtration, and the filtrate was concentrated to dryness under reduced pressure. The resulting residue was dissolved in acetone by heating followed by allowing the solution to cool. The precipitate formed upon cooling was recrystallized from ethanol to obtain 0.7 g of white amorphous 5-(2-morpholino-1-hydroxybutyl)-8-hydroxy-3,4-dihydrocarbostyril (I) hydrobromide 1/2 hydrate having a melting point of 183° - 185° C (with decomposition). The product thus obtained was confirmed by NMR and IR spectral analyses and elemental analysis.

Workup

  1. filtrationAfter completion of the reduction, the reaction mixture was filtered
  2. customto remove the catalysts
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. dissolutionThe resulting residue was dissolved in acetone
  6. temperatureby heating
  7. temperatureto cool
  8. customThe precipitate formed
  9. temperatureupon cooling
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-61c0b6825fcf493a87f7ea493d002383
Source dataset
uspto-grants-1976_11
Patent number
US03994901

Reaction notes

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