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

HRID 11144Notes

Reaction equation

HRID 11144 reaction equation
C[O:2][C:3]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:10]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:9][C:8]4[C:22](=[O:26])[NH:23][C:24](=[O:25])[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]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:9][C:8]4[C:22](=[O:26])[NH:23][C:24](=[O:25])[C:7]=4[C:6]=3[C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 118436889-Methoxy-5-phenylpyrrolo[3,4-c]carbazole-1,3(2h,6h)-dione

Product 1

HCID 118444789-hydroxy-5-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 89%

Procedure

Demethylation of 820 prepared as described in example 419 with BBr3 using the procedure described in example 80 gave (821) (89%), mp 335–345° C. 1H NMR δ [(CD3)2SO] 11.50 (s, 1H), 11.10 (s, 1H), 9.26 (d, J=2.4 Hz, 1H), 8.30 (d, J=2.4 Hz, 1H), 7.77–7.75 (m, 2H), 7.65–7.61 (m, 3H), 7.56–7.52 (m, 1H), 7.46 (d, J=8.7 Hz, 1H), 7.06 (dd, J=8.7, 2.4 Hz, 1H). Found: C, 72.71; H, 3.55; N, 8.16. C20H12N2O3 requires: C, 73.16; H, 3.68; N, 8.53.

Sources & evidence

ORD record
ord-b746986bccd04349ac80aca4a1d8e6ff
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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