Methyl 2,5-dimethoxyoxolane-2-carboxylate → 1-Cyclohexyl-7-(2-methoxycarbonyl-1-pyrrolyl)-6-nitro-2,3(1H,4H)-quinoxalinedione

HRID 861506Notes

Reaction equation

HRID 861506 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:19])[C:8](=[O:18])[N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].[CH3:23][O:24][C:25]([C:27]1(OC)[CH2:31][CH2:30][CH:29](OC)O1)=[O:26]>C(O)(=O)C>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([N+:20]([O-:22])=[O:21])=[C:2]([N:1]4[CH:29]=[CH:30][CH:31]=[C:27]4[C:25]([O:24][CH3:23])=[O:26])[CH:11]=3)[NH:6][C:7](=[O:19])[C:8]2=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 13152840Methyl 2,5-dimethoxyoxolane-2-carboxylateHCID 220970767-Amino-1-cyclohexyl-6-nitro-2,3(1H,4H)-quinoxalinedione2×

Product 1

HCID 220970791-Cyclohexyl-7-(2-methoxycarbonyl-1-pyrrolyl)-6-nitro-2,3(1H,4H)-quinoxalinedioneYield 78.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.5 g (14.8 mmol) of 7-amino-1-cyclohexyl-6-nitro-2,3(1H,4H)-quinoxalinedione (product 37b) and 3.5 g (14.8 mmol) of 2-methoxycarbonyl-2,5-dimethoxytetrahydrofuran in 75 ml of acetic acid were refluxed for 2 h. The mixture was poured into ice-water, and the precipitate was filtered off with suction to yield 4.8 g (78%) of the product. Melting point 293° C. (decomposition).

Workup

  1. filtrationthe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-00ed290441a84cd5ad9e73cc0d184b7e
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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