Aniline → 9-Bromo-5-phenylcarbamoyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52478Notes

Reaction equation

HRID 52478 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17](=[O:19])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

3

Reactant 2

HCID 6115AnilineHCID 99053359-bromo-5-carboxy-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 104310849-Bromo-5-phenylcarbamoyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 84%

Procedure

A procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxy-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (300 mg, 0.92 mmol) and aniline (93 mg, 1.0 mmol) to give 31 0 mg of the title compound (84%): mp>250° C.; 1H NMR (270 MHz, DMSO-d6) δ12.25 (s, 1H), 10.36 (s, 1H), 7.56 (d, 2H, J=8 Hz), 7.33 (t, 2H, J=8.0 Hz), 7.24 (bs, 1H), 7.22 (bs, 1H), 7.09 (t, 1H, J=8 Hz), 5.32~5.36 (m, 1H), 2.89 (dm, 1H, J=16.8 Hz), 2.58~2.81 (m, 2H), 2.05~2.22 (m, 1H).

Sources & evidence

ORD record
ord-116cce7299504660bbe21f2e43b111ed
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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