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Water → HCID 12899470, compound

HRID 569971
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Reaction equation

HRID 569971 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([OH:13])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4].[H-].[Na+].CN(C)[CH:18]=[O:19].Cl[CH2:22][CH:23]([OH:37])[CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:27][CH2:26]1.[OH2:38]>>[C:18]([OH:19])(=[O:37])[C:3]([OH:4])=[O:38].[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([O:13][CH2:22][CH:23]([OH:37])[CH2:24][N:25]3[CH2:30][CH2:29][N:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:27][CH2:26]3)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1822025-Hydroxy-1-methyl-3,4-dihydroquinolin-2-oneHCID 10037974HCID 10037974, compound

Product 1

HCID 12899470HCID 12899470, compound

Procedure

1.8 Grams of 1-methyl-5-hydroxy-3,4-dihydrocarbostyril and 1 g of NaH (50% in oil) are mixed with 30 ml of dimethylformamide. Then 2.6 g of 1-chloro-2-hydroxy-3-(4-phenylpiperazinyl)propane are added thereto at a room temperature and stirred at 70° to 80° C. for 3 hours. The reaction mixture is poured into water and the organic layer is extracted with chloroform. After removing chloroform by distillation, the thus obtained residue is dissolved in acetone and the pH of the solution is adjusted by adding an acetone solution of oxalic acid. The crystals precipitated are collected by filtration and recrystallized from methanol-acetone to obtain 2.8 g of 1-methyl-5-[2-hydroxy-3-(4-phenylpiperazinyl)-propoxy]-3,4-dihydrocarbostyril oxalate in the form of colorless crystals with a melting point of 220°-221° C. (decomp.).

Workup

  1. extractionthe organic layer is extracted with chloroform
  2. customAfter removing chloroform
  3. distillationby distillation
  4. dissolutionthe thus obtained residue is dissolved in acetone
  5. additionby adding an acetone solution of oxalic acid
  6. customThe crystals precipitated
  7. filtrationare collected by filtration
  8. customrecrystallized from methanol-acetone

Sources & evidence

ORD record
ord-7c76f1092db94eaeb2e5ac567a26ddb6
Source dataset
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04734416

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes