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

HRID 52550Notes

Reaction equation

HRID 52550 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.[CH3:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:26][C:25]3[CH:27]=[CH:28][C:22]([CH3:21])=[CH:23][CH:24]=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 7813p-ToluidineHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 442857069-Bromo-5-(p-tolylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 95.5%

Procedure

A procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (150 mg, 0.44 mmol) and p-methylaniline (107 mg, 1 mmol) to give 180 mg of the title compound (95%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.06 (s, 1H), 9.91 (s, 1H), 7.44 (d, 2H, J=8.6 Hz), 7.23 (bs, 1H), 7.17 (bs, 1H), 7.10 (d, 2H, J=8.6 Hz), 5.16~5.26 (m, 1H), 3.07 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1 Hz), 2.55~2.66 (m, 2H), 2.26 (s, 3H), 2.09 (dm, 1H, J=13.5 Hz), 1.80~1.94 (m, 1H).

Sources & evidence

ORD record
ord-582f14fd1f7f46a4ba81480215f8baed
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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