8-(Benzyloxy)-4-(2-chlorophenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione → 8-(Benzyloxy)-4-(2-chlorophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11123Notes

Reaction equation

HRID 11123 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:34][CH3:35])=[CH:11][C:12]2[C:13]3[CH:14]4[C:31](=[O:32])[NH:30][C:29](=[O:33])[CH:15]4[CH:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:28])[CH2:17][C:18]=3[NH:19][C:20]=2[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:10]([O:34][CH3:35])=[CH:11][C:12]2[C:13]3[C:14]4[C:31](=[O:32])[NH:30][C:29](=[O:33])[C:15]=4[C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:28])=[CH:17][C:18]=3[NH:19][C:20]=2[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 867602138-(Benzyloxy)-4-(2-chlorophenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione

Product 1

HCID 867602158-(Benzyloxy)-4-(2-chlorophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 93%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

Aromatisation of (161) prepared as described in example 261 with manganese dioxide using the procedure described in example 79 gave the carbazole (162) (93%) as an orange powder, mp 260–264° C. 1H NMR δ [(CD3)2SO] 11.86 (s, 1H), 11.01 (s, 1H), 8.43 (s, 1H), 7.58–7.34 (m, 10H), 7.26 (s, 1H), 5.26 (s, 2H), 3.91 (s, 3H). Found: C, 69.65; H, 3.84; N, 5.61. C28H19ClN2O4 requires C, 69.64; H, 3.97; N, 5.80.

Sources & evidence

ORD record
ord-d22ddd8026f748649d3dd6a766adff05
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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