4-Nitroaniline → 9-Bromo-5-(p-nitrophenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52531Notes

Reaction equation

HRID 52531 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](O)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[N+:21]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)([O-:23])=[O:22]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:28][C:27]3[CH:29]=[CH:30][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=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 74754-NitroanilineHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 442855219-Bromo-5-(p-nitrophenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 35%

Procedure

A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro- 1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (170 mg, 0.5 mmol) and p-nitroaniline (70 mg, 0.51 mmol) to give 80 mg of the title compound (35%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.07 (s, 1H), 10.65 (s, 1H), 8.23 (d, 2H, J=9.2 Hz), 7.30 (d, 2H, J=9.2 Hz), 7.24 (bs, 1H), 7.18 (bs, 1H), 5.20~5.29 (m, 1H), 3.04 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1 Hz), 2.68 (d, 2H, J=7.3 Hz), 2.11 (dm, 1H, J=13.5 Hz), 1.82~1.97 (m, 1H).

Sources & evidence

ORD record
ord-e6077b06621b41579546fe5604859f82
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

Loading…