Reacción #11148

Ecuación de reacción

potassium acetate

ethyl acetate

4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

→

9-Hydroxy-6-(3-hydroxypropyl)-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Rendimiento 51.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas reacted for 7 h
2. 2
   FiltraciónThe catalyst was filtered off
3. 3
   Concentraciónthe filtrate concentrated to dryness
4. 4
   OtroThe residue was partitioned between ethyl acetate and water
5. 5
   Otrothe organic solution was dried
6. 6
   Otrothe drying agent was removed
7. 7
   Concentraciónthe solution was concentrated to dryness
8. 8
   Otrochromatographed on silica
9. 9
   LavadoElution with ethyl acetate/petroleum ether (2:1)

Procedimiento

4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OH) (106) (0.20 g, 0.44 mmol) prepared as described in example 59, potassium acetate (0.20 g) and 5% Pd/C in a solution of ethyl acetate (25 ml) and methanol 1:1 (25 mL) under a atmosphere of hydrogen at 60 psi was reacted for 7 h. The catalyst was filtered off and the filtrate concentrated to dryness. The residue was partitioned between ethyl acetate and water and the organic solution was dried, the drying agent was removed and the solution was concentrated to dryness and chromatographed on silica. Elution with ethyl acetate/petroleum ether (2:1) gave 9-Hydroxy-6-(3-hydroxypropyl)-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-methoxyphenyl, R10═CH2CH2CH2OH) (107) in a yield of 51% as an orange powder (from THF/petroleum ether), mp 296–300° C. 1H NMR δ [(CD3)2SO] 10.93 (br s, 1H), 9.31 (br s, 1H), 8.38 (d, J=2.4 Hz, 1H), 7.69 (s, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.42 (m, 1H), 7.35 (dd, J=7.5, 1.7 Hz, 1H), 7.13–7.08 (m, 2H), 7.05 (dd, J=7.2, 7.2 Hz, 1H), 4.62 (t, J=4.8 Hz, 1H), 4.48 (t, J=6.8 Hz, 2H), 3.68 (s, 3H), 3.40 (m, 2H), 1.90 (m, 2H). Found: C, 69.29; H, 4.90; N, 6.54. C24H20N2O5 requires C, 69.22; H, 4.84; N, 6.73.

Fuente