Reaktion #1144836

Reaktionsgleichung

benzyl bromide

sodium hydride

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

→

title compound

Ausbeute 81.9%

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

Ausbeute 81.9%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeroom temperature overnight
2. 2
   SonstigeThe mixture is partitioned between water and CH2Cl2
3. 3
   SonstigeThe layers are separated
4. 4
   Waschenthe organic layer washed with water (200 mL)
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue is triturated in hexanes
7. 7
   Filtrationfiltered

Vorschrift

To a slurry of 60% sodium hydride (0.76 g, 19.6 mmol) in DMF (20 mL) is added 6-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one (3.84 g, 17.8 mmol) over a period of 5 minutes and benzyl bromide (2.4 mL, 19.6 mmol). The mixture is heated to 50° C. for 1 hour then room temperature overnight. The mixture is partitioned between water and CH2Cl2. The layers are separated and the organic layer washed with water (200 mL) and concentrated. The residue is triturated in hexanes and filtered to give 4.45 g (80%) of the title compound; mp 174-175° C., IR (drift) 2939, 1633, 1484, 1467, 1448, 1349, 1276, 1242, 1159, 1130, 1099, 854, 791, 762, 710 cm−1. 1H NMR (DMSO-d6) δ2.1, 2., 2.93, 3.75, 5.44, 6.77, 7.09, 7.28, 7.39, 7.51; Anal. Calcd for C20H19NO2: C, 78.66; H, 6.27; N, 4.59. Found: C, 78.45; H, 6.31; N, 4.58.

Quelle