Reaktionsgleichung
N#N.[CH3:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[NH:6][CH:5]=1.[O-:15]S(OOS([O-])(=O)=O)(=O)=O.[Na+].[Na+].O>CS(C)=O>[O:14]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([CH:3]=[O:15])=[CH:5][NH:6]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
In an apparatus equipped with a mechanical stirrer (N2 gas), 135 g (848 mmol) of 4-methyl-2H-isoquinolin-1-one in 2.0 l of DMSO are heated to 50° C. After removing the oil bath, 108 g (447 mmol) of Cu(NO3)2.3H2O are added. Then, whilst cooling, 432 g (1.81 mol) of Na2S2O8 are added in portions, and finally 162 g (1.91 mol) of NaNO3. After stirring for 2 h at 50° C., the mixture is cooled to 10° C., mixed with 4 l of water and stirred for 10 min. 1-oxo-1,2-dihydro-isoquinoline-4-carbaldehyde can be filtered from the light green suspension and washed with water; m.p. 222-223° C. The filtrate is extracted 3 more times with EtOAc. The EtOAc phases are washed with water (3×) and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography of the residue (SiO2, methylene chloride/toluene/acetone 2:2:1) yields further 1-oxo-1,2-dihydro-isoquinoline-4-carbaldehyde.
Aufarbeitung
- additionare added
- temperatureThen, whilst cooling
- temperaturethe mixture is cooled to 10° C.
- stirringstirred for 10 min
- filtration1-oxo-1,2-dihydro-isoquinoline-4-carbaldehyde can be filtered from the light green suspension
- washwashed with water
- extractionThe filtrate is extracted 3 more times with EtOAc
- washThe EtOAc phases are washed with water (3×) and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated by evaporation
Quellen und Nachweise
- ORD-Eintrag
- ord-8340d5c337cb4981b7fe0661e52e1217
- Quelldatensatz
- uspto-grants-2004_03
- Patentnummer
- US06706731B2
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