Hydrochloric Acid → 6-(3-Hydroxypropyl)-9-methoxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11047Notes

Reaction equation

HRID 11047 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[CH2:23][CH:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])[CH:21]3[C:33](=[O:37])[NH:34][C:35](=[O:36])[CH:20]3[C:19]=2[C:18]2[CH:17]=[C:16]([O:38][CH3:39])[CH:15]=[CH:14][C:13]1=2)(C(C)(C)C)(C)C.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.Cl>C1COCC1.CO>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[CH:23]=[C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])[C:21]3[C:33](=[O:37])[NH:34][C:35](=[O:36])[C:20]=3[C:19]=2[C:18]2[CH:17]=[C:16]([O:38][CH3:39])[CH:15]=[CH:14][C:13]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 867601946-(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)-9-methoxy-4-(2-methoxyphenyl)-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2h, 3ah)-dione

Product 1

HCID 867601936-(3-Hydroxypropyl)-9-methoxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The reaction of 6-(3-{[tert-Butyl(dimethyl)silyl)oxy}propyl)-9-methoxy-4-(2-methoxyphenyl)-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=2-methoxyphenyl; R10═CH2CH2CH2OSiMe2t-Bu) prepared as described in example 52 with DDQ using the procedure described in example 70 followed reaction with 2N HCl in THF/methanol gave 6-(3-Hydroxypropyl)-9-methoxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-methoxyphenyl, R10═CH2CH2CH2OH) (100) in a 72% yield as an orange powder; mp 223–225° C. 1H NMR δ [(CD3)2SO] 10.99 (br s, 1H), 8.53 (d, 2.6 Hz, 1H), 7.74 (s, 1H), 7.67 (d, J=8.9 Hz, 1H), 7.45–7.40 (m, 1H), 7.36 (dd, J=7.4, 1.7 Hz, 1H), 7.29 (dd, J=8.9, 2.7 Hz, 1H), 7.11 (d, J=8.1 Hz, 1H), 7.06 (dd, J=7.2, 7.2 Hz, 1H), 4.63 (t, J=4.8 Hz, 1H), 4.52 (t, J=6.9 Hz, 2H), 3.90 (s, 3H), 3.69 (s, 3H), 3.40 (m, 2H), 1.91 (m, 2H). Found: C, 69.55; H, 5.31; N, 6.30. C25H22N2O5 requires C69.76; H, 5.15; N, 6.51.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-1860bb7aaf754f549fac96415c1c1103
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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