Aniline → 6-(3-Anilinopropyl)-9-Hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11096Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]3[C:24](=[O:28])[NH:25][C:26](=[O:27])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:29])[CH:8]=[CH:7][C:6]1=2.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[NH:30]([CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]3[C:24](=[O:28])[NH:25][C:26](=[O:27])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:29])[CH:8]=[CH:7][C:6]1=2)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Reactant 2

HCID 6115Aniline

HCID 867602016-(3-Bromopropyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 219804066-(3-Anilinopropyl)-9-Hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 38%

Procedure

Bromide (204) (75 mg, 0.17 mmol) prepared as described in example 173 was reacted with aniline according to the procedure described in example 179 except that the reaction was performed at room temperature for 20 h, to give aniline (217) (30 mg, 38%) as a yellow powder, mp 240° C. (dec). 1H NMR δ [(CD3)2SO] 11.04 (br s, 1H), 9.33 (s, 1H), 8.40 (d, J=2.4 Hz, 1H), 7.78 (s, 1H), 7.59 (d, J=8.9 Hz, 1H), 7.48 (m, 2H), 7.42 (m, 3H), 7.10 (dd, J=8.8, 2.4 Hz, 1H), 7.05 (m, 2H), 6.52 (m, 3H), 5.70 (t, J=5.3 Hz, 1H), 4.59 (t, J=6.8 Hz, 2H), 2.98 (t, J=6.3 Hz, 2H), 2.07 (m, 2H). Found: C, 74.00; H, 5.22; N, 8.76. C29H23N3O3.1/2H2O requires: C, 74.03; H, 5.14; N, 8.93.

Sources & evidence

ORD record: ord-aece01f510ab41f1a3cba2126cfe5d57
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094798B1

Reaction notes

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