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Triphenylphosphine → 1-Aminoisoquinoline-7-carbonitrile

HRID 636969
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 636969
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OS(C(F)(F)F)(=O)=O)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:39][N:40]1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[C-]#N.[Zn+2].[C-]#N>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:39]#[N:40])[CH:10]=2)[CH:5]=[CH:4][N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 13387N-methyl-2-pyrrolidoneHCID 54109345Trifluoromethanesulfonic acid 1-amino-isoquinolin-7-yl ester

Produkt 1

HCID 226658481-Aminoisoquinoline-7-carbonitrileAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator
HCID 167845
palladium(II) acetate
Katalysator

Versuchsvorschrift

Palladium acetate (0.9 g) was added to a heated mixture of trifluoromethanesulfonic acid 1-amino-isoquinolin-7-yl ester (5.8 g), zinc cyanide (2.3 g) and triphenylphosphine (1.0 g) in 75 mL of N-methyl-pyrrolidone at 190° C. (exothermic!). Stirring was continued at 190° C. for 2 h. Precipitated material was removed by filtration and discarded. Ethyl acetate was added and the organic mixture washed with 2N aqueous ammonia, water and brine and dried (Na2SO4). Filtration and concentration afforded a brownish oil, which was purified by silica chromatography (ethyl acetate/isohexane=3/7, 4/6, 5/5, 6/4, 7/3, 8/2) to give 3.2 g (94%) of the title compound as yellow crystals. M.p. 183-186° C.

Aufarbeitung

  1. customPrecipitated material was removed by filtration
  2. additionEthyl acetate was added
  3. washthe organic mixture washed with 2N aqueous ammonia, water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and concentration
  6. customafforded a brownish oil, which
  7. customwas purified by silica chromatography (ethyl acetate/isohexane=3/7, 4/6, 5/5, 6/4, 7/3, 8/2)

Quellen und Nachweise

ORD-Eintrag
ord-8527cd480a8a4198bbe58ddb67de51e0
Quelldatensatz
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06194409B1

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