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8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone → 8-Cyclohexylcarbonyloxy-5-(1-hydroxy-2-isopropylaminobutyl)carbostyril

HRID 27779
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 27779
[OH:1][CH:2]([C:10]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]2[C:11]=1[CH:12]=[CH:13][C:14](=[O:21])[NH:15]2)[CH:3]([NH:6][CH:7]([CH3:9])[CH3:8])[CH2:4][CH3:5].C[O-:23].[Na+].N1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=CC1=O>CO>[CH:30]1([C:29]([O:20][C:17]2[CH:18]=[CH:19][C:10]([CH:2]([OH:1])[CH:3]([NH:6][CH:7]([CH3:9])[CH3:8])[CH2:4][CH3:5])=[C:11]3[C:16]=2[NH:15][C:14](=[O:21])[CH:13]=[CH:12]3)=[O:23])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1
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Komponenten

5

Edukt 3

HCID 49168-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinoneHCID 60382-HydroxyquinolineHCID 10942334Sodium Methoxide

Produkt 1

HCID 233420758-Cyclohexylcarbonyloxy-5-(1-hydroxy-2-isopropylaminobutyl)carbostyril

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5.8 g of 5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril was dissolved in 100 ml of methanol, and a methanolic solution of 10% sodium methylate was added to the resulting solution in an equimolar amount relative to the starting carbostyril compound. The mixture was concentrated to dryness and the resulting residue was dissolved in 100 ml of dimethylformamide. 2.9 g of cyclohexanecarboxylic acid chloride was then added while cooling with ice-water and the mixture was stirred for one hour at a temperature of 0° C. The precipitate formed was separated by filtration and washed successively with dimethylformamide and diethyl ether to obtain 4.0 g of 8-cyclohexylcarbonyloxy-5-(1-hydroxy-2-isopropylaminobutyl)carbostyril having a melting point of 186.5°-187.5° C. (after recrystallization from chloroform-diethyl ether).

Aufarbeitung

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutionthe resulting residue was dissolved in 100 ml of dimethylformamide
  3. addition2.9 g of cyclohexanecarboxylic acid chloride was then added
  4. temperaturewhile cooling with ice-water
  5. customThe precipitate formed
  6. customwas separated by filtration
  7. washwashed successively with dimethylformamide and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f3590321f0f643f4a964e0c3575330c3
Quelldatensatz
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04223137

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