Phosphoric Acid → Vesnarinone

HRID 1649241

반응식

HRID 1649241 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 5663Vesnarinone수율 71.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-41d2bcafaa9446f1a222956d6f3d9107
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04415572

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