Reaktion #11200

Reaktionsgleichung

methyl ether

N-[2-(Dimethylamino)ethyl]-3-(9-methoxy-1,3-dioxo-4-phenyl-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanamide

ammonia

→

N-[2-(Dimethylamino)ethyl]-3-(9-hydroxy-1,3-dioxo-4-phenyl-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanamide

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   SonstigeThe organic layer was dried
4. 4
   Sonstigethe drying agent was removed
5. 5
   Einengenthe solution was concentrated to dryness
6. 6
   SonstigeCrystallization from ethyl acetate/hexane

Vorschrift

Reaction of methyl ether (247) (70 mg, 0.14 mmol) prepared as described in example 207 according to the procedure described in example 81, except that the reaction mixture was diluted with water, basified by the addition of concentrated ammonia and extracted with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetate/methanol/triethylamine (1:0:0 to 3:1:trace). Crystallization from ethyl acetate/hexane then gave amide (254) (35 mg, 53%) as an orange powder, mp 176–180° C. 1H NMR δ [(CD3)2SO] 11.06 (br s, 1H), 9.35 (br s, 1H), 8.39 (d, J=2.5 Hz, 1H), 7.77 (s, 1H), 7.74 (t, J=5.6 Hz, 1H), 7.66 (m, 2H), 7.53 (d, J=8.8 Hz, 1H), 7.48 (m, 3H), 7.12 (dd, J=8.8, 2.5 Hz, 1H), 4.69 (t, J=6.4 Hz, 2H), 2.94 (m, 2H), 2.58 (t, J=6.4 Hz, 2H), 1.91 (s, 6H), 1.87 (m, 2H). Found: C, 66.87; H, 5.83; N, 11.47. C27H26N4O4.3/4H2O requires: C, 67.00; H, 5.73; N, 11.57.

Quelle