Acetic Acid → 2-(Prop-2-yn-1-yl)isoquinolin-1(2H)-one

HRID 1032776

Reaktionsgleichung

Reaktionsgleichung von HRID 1032776
[C:1]1([C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][NH:3]1)=[O:2].[K].[CH3:13][C:14](C)([O-])[CH3:15].C(Br)C#C.C(O)(=O)C>CN(C)C=O.O>[CH2:15]([N:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1]1=[O:2])[C:14]#[CH:13]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 7842Propargyl bromideHCID 102841(2H)-IsoquinolinoneHCID 50987170Potassium tertbutoxide

Produkt 1

HCID 148519532-(Prop-2-yn-1-yl)isoquinolin-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1 g (7 mmol) of isocarbostyril in 40 ml of dimethylformamide was treated with 0.86 g (7.7 mmol) of potassium-tert.-butoxide. After stirring under nitrogen for 30 minutes, 0.7 ml of propargyl bromide was added and stirring at room temperature was continued for 1 hour. The reaction mixture was acidified with acetic acid and diluted with water. The precipitated product was filtered off, washed with water and sucked dry. The residue was purified by chromatography over 30 g of silica gel using 5% (v/v) of ethanol in methylene chloride and crystallization from ether to give colorless crystals of 2-(2-propynyl)-1(2H)-isoquinolinone with m.p. 104°-105°. contains about. 0.125 molar amounts of H2O.

Aufarbeitung

  1. stirringstirring at room temperature
  2. waitwas continued for 1 hour
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water
  5. customsucked dry
  6. customThe residue was purified by chromatography over 30 g of silica gel using 5% (v/v) of ethanol in methylene chloride and crystallization from ether

Quellen und Nachweise

ORD-Eintrag
ord-47355f03d7214ad3a0662f1cc36ceef2
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04959361

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