Boron tribromide → 9-Hydroxy-5-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11140Notes

Reaction equation

HRID 11140 reaction equation
C[O:2][C:3]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:10]([CH3:16])=[C:9]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:8]4[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:7]=4[C:6]=3[C:5]=2[CH:4]=1.B(Br)(Br)Br>>[OH:2][C:3]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:10]([CH3:16])=[C:9]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:8]4[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:7]=4[C:6]=3[C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 118436839-Methoxy-5-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 118443469-Hydroxy-5-methyl-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 90%

Procedure

Demethylation of (803) prepared as described in example 406 with BBr3 using the procedure described in example 69 gave (804) (90%), mp 270–280° C. 1H NMR δ [(CD3)2SO] 11.60 (s, 1H), 10.82 (s, 1H), 9.22 (s, 1H), 8.31 (d, J=2.0 Hz, 1H), 7.47–7.42 (m, 4H), 7.36–7.23 (m, 2H), 7.06 (dd, J=8.7, 2.0 Hz, 1H), 2.32 (s, 3H). EIMS found M+:342.1005. C21H14N2O3 requires: 342.1004.

Sources & evidence

ORD record
ord-5a7efcaac9d44119a09dedaf3e502208
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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