6-(2-Hydroxy-3-methoxypropyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione → HCID 21980594, compound
Reaction equation
[OH:1][CH:2]([CH2:30][O:31]C)[CH2:3][N:4]1[C:16]2[CH:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]3[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:12]=3[C:11]=2[C:10]2[CH:9]=[C:8]([O:28]C)[CH:7]=[CH:6][C:5]1=2>C(OCC)(=O)C.CCCCCC>[OH:1][CH:2]([CH2:30][OH:31])[CH2:3][N:4]1[C:16]2[CH:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:13]3[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:12]=3[C:11]=2[C:10]2[CH:9]=[C:8]([OH:28])[CH:7]=[CH:6][C:5]1=2Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Demethylation of alcohol (225) (96 mg, 0.22 mmol) prepared as described in example 290 employing the procedure described in example 80 was followed by chromatography on silica eluting with ethyl acetate/hexane (4:1). Crystallisation from ethyl acetate/hexane gave phenol (226) (28 mg, 31%) as an orange/yellow powder, mp 290–295° C. 1H NMR δ [(CD3)2SO] 11.04 (br s, 1H), 9.30 (s, 1H), 8.40 (d, J=2.4 Hz, 1H), 7.79 (s, 1H), 7.63 (m, 2H), 7.55 (d, J=8.8 Hz, 1H), 7.47 (m, 3H), 7.11 (dd, J=8.8, 2.4 Hz, 1H), 5.00 (d, J=5.4 Hz, 1H), 4.86 (t, J=5.4 Hz, 1H), 4.51 (dd, J=3.8, 14.9 Hz, 1H), 4.35 (dd, J=7.5, 14.9 Hz, 1H), 3.89 (m, 1H), 3.41 (m, 2H). Found: C, 67.94; H, 4.69; N, 6.50. C23H18N2O5.1/4H2O requires: C, 67.89; H, 4.58; N, 6.88.