Reacción #1144837

Ecuación de reacción

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

p-dioxane

lithium bromide

lithium carbonate

→

title compound

Rendimiento 73.0%

9-Benzyl-6-methoxy-9H-carbazol-4-ol

Rendimiento 73.0%

Disolventes

ethylene glycol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture is partitioned between water and Et2O
2. 2
   OtroThe layers are separated
3. 3
   Lavadothe organic layer washed with water (100 mL)
4. 4
   SecadoThe ether layer is dried over anhydrous sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   workup.DISSOLUTIONThe residue is dissolved in DMF (50 mL) to which
8. 8
   TemperaturaThe mixture is heated at 120° C. for 5 h
9. 9
   OtroThe mixture is partitioned between water and ethyl acetate
10. 10
    OtroThe layers are separated
11. 11
    Lavadothe organic layer washed twice with water (200 mL)

Procedimiento

To a mixture of 9-benzyl-6-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one (4.23 g, 13.85 mmol) in ethylene glycol: p-dioxane ((1:1) 150 mL) is added copper (II) chloride (9.31 g, 69.26 mmol). The mixture is heated at 80° C. for 30 minutes. The mixture is partitioned between water and Et2O. The layers are separated and the organic layer washed with water (100 mL). The ether layer is dried over anhydrous sodium sulfate, filtered and concentrated. The residue is dissolved in DMF (50 mL) to which is added lithium bromide (2.45 g, 28.3 mmol) and lithium carbonate (2.09 g, 28.3 mnmol). The mixture is heated at 120° C. for 5 h. The mixture is partitioned between water and ethyl acetate. The layers are separated and the organic layer washed twice with water (200 mL). Column chromatography (250 mL) silica gel using ethyl acetate/ hexanes (20/80) gave 2.5 g (73%) of the title compound; IR (drift) 3471, 1482, 1469, 1450, 1328, 1198, 1171, 1144, 805, 799, 780, 745, 724, 717, 701 cm−1. 1H NMR (DMSO-d6) δ3.82, 5.54, 6.56, 6.97), 7.14, 7.23, 7.43, 7.72; Anal. Calcd for C20H17NO2: C, 79.18; H, 5.65; N, 4.62. Found: C, 78.99; H, 5.75; N, 4.63.

Fuente