Reaktion #1144835

Reaktionsgleichung

4-methoxyphenyl hydrazine

1,3 cyclohexanedione

→

title compound

Ausbeute 65.5%

6-Methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one

Ausbeute 65.5%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is refluxed for 30 minutes
2. 2
   SonstigeThe toluene is removed under reduced pressure
3. 3
   Sonstigethe residue triturated in CH2Cl2: CH3OH (95:5)
4. 4
   FiltrationA white solid is filtered

Vorschrift

To a mixture of 4-methoxyphenyl hydrazine (0.359 g, 2.06 mmol) in toluene (30 mL) is added 1,3 cyclohexanedione (0.231 g, 2.06 mmol). The mixture is refluxed for 30 minutes. The toluene is removed under reduced pressure and the residue triturated in CH2Cl2: CH3OH (95:5). A white solid is filtered to give 0.2903 g (65%) of the title compound; IR (drift) 3160, 3141, 3114, 3064, 1619, 1588, 1474, 1434, 1277, 1215, 1140, 1015, 844, 802, 791 cm−1. MS (ESI+) for C13H13N1O2 m/z 216 (M+H)+. 1H NMR (DMSO-d6) δ2.08, 2.39, 2., 3.74, 6.74, 7.25, 7.43; Anal Calcd for C13H13NO2: C, 72.54; H, 6.09; N, 6.51. Found: C, 71.48; H, 6.06; N, 6.45.

Quelle