3-Aminophenol → HCID 67928892, Verbindung
Reaktionsgleichung
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[N+](C1C=CC([O:16][C:17]([O:19][CH:20]2[CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:24][C:23]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[N:22][CH2:21]2)=O)=CC=1)([O-])=O>CN(C)C=O>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][C:17]([O:19][CH:20]2[CH:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:24][C:23]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[N:22][CH2:21]2)=[O:16])[CH:7]=[CH:6][CH:5]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
3-Aminophenol (1 g) is added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of (5RS, 6SR)-5-(4-nitrophenoxycarbonyloxy)-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazine (2.5 g) in anhydrous dimethylformamide (30 cc). The solution obtained is heated at 70° C. for 5 hours, then cooled to a temperature in the region of 20° C. and poured into distilled water (300 cc). The mixture is extracted with dichloromethane (2×150 cc). The organic phases are combined, washed with distilled water (3×20 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The oil obtained is purified by chromatography on silica (0.063-0.2 mm; 100 g) contained in a column 2 cm in diameter [eluent: cyclohexane/ethyl acetate/triethylamine (60:35:5 by volume)], collecting 25-cc fractions. The fractions 10 to 17 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in diisopropyl ether, (5RS, 6SR)-5-(3-hydroxyphenylcarbamoyloxy)-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazine (1.1 g), m.p. 170° C., is obtained.