4-Chlorobenzoic Acid → 9-(4-Chlorobenzoyl)-1,4,7,8,9,10-hexahydro-6-nitropyrido[3,4-f]quinoxaline-2,3-dione

HRID 1106442Notes

Reaction equation

HRID 1106442 reaction equation
[N+:1]([C:4]1[C:5]2[CH2:19][CH2:18][NH:17][CH2:16][C:6]=2[C:7]2[NH:8][C:9](=[O:15])[C:10](=[O:14])[NH:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](O)=[O:38])=[CH:35][CH:34]=1>>[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([N:17]2[CH2:18][CH2:19][C:5]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:12]4[NH:11][C:10](=[O:14])[C:9](=[O:15])[NH:8][C:7]=4[C:6]=3[CH2:16]2)=[O:38])=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 63184-Chlorobenzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 154347081,4,7,8,9,10-Hexahydro-6-nitropyrido[3,4-f]quinoxaline-2,3-dione

Product 1

HCID 212530619-(4-Chlorobenzoyl)-1,4,7,8,9,10-hexahydro-6-nitropyrido[3,4-f]quinoxaline-2,3-dioneYield 104.4%

Procedure

The 7-nitroquinoxalinedione from Example 31 (100 mg, 0.38 mmol) was treated with the CDI adduct of 4-chlorobenzoic acid (0.57 mmol) by a procedure similar to that in Example 32 to give a yellow solid (159 mg, 99% yield). mp=280-283° C. (dec.). MS(CI) M+1 401; CHN calc'd for C18H13ClN4O5 within ±0.4.

Sources & evidence

ORD record
ord-f3d3ac005b644ad3bedfd92f69a12922
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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