Ethanol → 6-{4-[3-(4-Chlorobenzoyl)-3-hydroxyliminopropyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril

HRID 1460680Notes

Reaction equation

HRID 1460680 reaction equation
ClC1C=CC(C(CC[C:10]2([C:21]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[O:22])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=C[CH:17]=3)[NH:12]C2=O)=O)=CC=1.[ClH:31].[NH2:32][OH:33].[C:34]([O-:37])(=O)[CH3:35].[Na+].[CH2:39]([OH:41])[CH3:40]>O>[Cl:31][C:13]1[CH:18]=[CH:17][C:40]([C:39]([C:19](=[N:32][OH:33])[CH2:10][CH2:21][N:26]2[CH2:25][CH2:24][N:23]([C:21]([C:10]3[CH:19]=[C:18]4[C:13](=[CH:14][CH:15]=3)[NH:12][C:34](=[O:37])[CH2:35][CH2:17]4)=[O:22])[CH2:28][CH2:27]2)=[O:41])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 1317170952-(4-Chlorobenzoyl)ethyl[-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril

Product 1

HCID 881243866-{4-[3-(4-Chlorobenzoyl)-3-hydroxyliminopropyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.7 Grams of 6-{4-[2-(4-chlorobenzoyl)ethyl[-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril, 0.83 g of hydroxylamine hydrochloride and 2.29 g of sodium acetate were dissolved in 40 ml of ethanol and 20 ml of water, and the solution was stirred overnight at room temperature. Then the reaction mixture was concentrated under reduced pressure, then the residue thus obtained was extracted with chloroform, the extract was dried with anhydrous sodium carbonate, then the solvent was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol =50:1), then recrystallized from ethanol to yield 1.2 g of 6-{4[-3-(4-chlorobenzoyl)-3-hydroxyliminopropyl]-1-piperazinylcarbonyl}-3,4-dihydrocarbostyril. White powdery substance. Melting point: 207° C.-209° C. (decomp.).

Workup

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. extractionwas extracted with chloroform
  4. dry with materialthe extract was dried with anhydrous sodium carbonate
  5. customthe solvent was removed by evaporation
  6. customThe residue thus obtained
  7. customwas purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol =50:1)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8cf757d0714b4a5aa2e8e9b21c6197bc
Source dataset
uspto-grants-1991_12
Patent number
US05071856

Reaction notes

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