Water → HCID 12899470, compound

HRID 621572Notes

Reaction equation

HRID 621572 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]

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 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 colleced by filtration and recrystallization 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 colleced by filtration and recrystallization from methanol-acetone

Sources & evidence

ORD record
ord-2f344fdd058f4b188832ca1226c6661b
Source dataset
uspto-grants-1989_04
Patent number
US04824840

Reaction notes

Loading…