O-Allylhydroxylamine → 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde-O-allyl oxime
Reaktionsgleichung
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O.[CH2:19]([O:22][NH2:23])[CH:20]=[CH2:21]>C(OCC)(=O)C>[CH2:19]([O:22][N:23]=[CH:13][C:12]1[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=1[NH:10][C:3]1[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[Cl:1])[CH:20]=[CH2:21]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution in 3:1 ethanol-pyridine of 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde, prepared as in Example 1, steps 1-2, and O-allyl hydroxylamine(1.3 eq) was heated at reflux for 2 days. The reaction mixture was poured into ethyl acetate and the mixture was extracted with 10% aqueous HCl. Chromatography on silica gel (20% CH2Cl2 /hexanes) gave 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde-O-allyl oxime (1.13 g, 94%).