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Water → HCID 12777809, Verbindung

HRID 2390023
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2390023
CON(C)[C:4]([CH2:6][C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=O.[C:18]1([Mg]Br)C=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH2:26]>C1COCC1>[C:6]([C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:26])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 131729961HCID 131729961, VerbindungHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 12777809HCID 12777809, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under an argon gas stream, 168 mg of N-methoxy-N-methylisoquinoline-3-carboxyamide was dissolved in 1 mL of anhydrous THF, followed by stirring under cooling with ice. To the reaction liquid was slowly added 0.8 mL of phenyl magnesium bromide (1 mol/L THF solution), followed by continuously stirring for 30 minutes. Water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with diluted hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography (chloroform alone) to obtain 154 mg (yield 77%) of a title compound as a yellow oily substance.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. customTo the reaction liquid
  3. stirringby continuously stirring for 30 minutes
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with diluted hydrochloric acid and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customwas purified by silica gel chromatography (chloroform alone)

Quellen und Nachweise

ORD-Eintrag
ord-ac6f507ba7934ea3a6b7c75b7ecf6167
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08273766B2

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