Phosphoric Acid → Vesnarinone

HRID 1649241

Reaction equation

HRID 1649241 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.O[CH2:14][CH2:15][N:16]([CH2:29][CH2:30]O)[C:17](=[O:28])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1.P(=O)(O)(O)O.[OH-].[Na+]>O>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[O:24][CH3:25])[C:17]([N:16]1[CH2:15][CH2:14][N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]3)[CH2:30][CH2:29]1)=[O:28]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 20144316N,N-bis(2-hydroxyethyl)-3,4-dimethoxybenzamide

Product 1

HCID 5663VesnarinoneYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.7 g of 6-amino-3,4-dihydrocarbostyril, 5.9 g of N,N-bis(2-hydroxyethyl)-3,4-dimethoxybenzamide and 8.6 g of 85% phosphoric acid was reacted at 165° to 175° C. for 4.5 hours while stirring. After allowing to cool, to the reaction mixture was added dropwise about 50 ml of water to dissolve. The solution was neutralized with an aqueous 48% sodium hydroxide solution and extracted with chloroform. After drying the extract over potassium carbonate, chloroform was distilled off. Recrystallization of the residue from ethanol-chloroform gave 4.7 g of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 238°-239.5° C., colorless granules.

Workup

  1. customwas reacted at 165° to 175° C. for 4.5 hours
  2. temperatureto cool, to the reaction mixture
  3. dissolutionto dissolve
  4. extractionextracted with chloroform
  5. customAfter drying the
  6. extractionextract over potassium carbonate, chloroform
  7. distillationwas distilled off
  8. customRecrystallization of the residue from ethanol-chloroform

Sources & evidence

ORD record
ord-41d2bcafaa9446f1a222956d6f3d9107
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Linked notes

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