Dimethylformamide → N-(3-(tert-Butyldimethylsilyloxy)propyl)-3-nitroquinolin-4-amine
Reaktionsgleichung
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1O)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].CN(C=O)C.S(Cl)(Cl)=O.[Si:24]([O:31][CH2:32][CH2:33][CH2:34][NH2:35])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(Cl)Cl.CCN(CC)CC>[Si:24]([O:31][CH2:32][CH2:33][CH2:34][NH:35][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])([C:27]([CH3:29])([CH3:30])[CH3:28])([CH3:26])[CH3:25]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred solution of 3-nitro-quinolin-4-ol (5 g) in DCM (70 mL) was added DMF (2.3 mL) then thionyl chloride (2.1 mL) and the reaction mixture was refluxed for 3 h. The solution was cooled to 0° C. and 3-{[tert-butyl(dimethyl)silyl]oxy}propan-1-amine (6 g) was added followed by dropwise addition of Et3N (12 mL). The reaction mixture was stirred at rt for 2 h, then partitioned between DCM and saturated NaHCO3 solution. The organic layer was washed with water, dried, and the solvent evaporated under reduced pressure. The residue was triturated with iso-hexane to leave the subtitle compound (8.7 g).
Aufarbeitung
- custompartitioned between DCM and saturated NaHCO3 solution
- washThe organic layer was washed with water
- customdried
- customthe solvent evaporated under reduced pressure
- customThe residue was triturated with iso-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-e9e810d5960d450b93f1a952b57f5c4e
- Quelldatensatz
- uspto-grants-2013_05
- Patentnummer
- US08436178B2
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