Sulfuric Acid → 6-Amino-1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedione

HRID 861487Notes

Reaction equation

HRID 861487 reaction equation
[CH:1]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([NH:20]C(=O)C(OCC)=O)=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[NH:10][C:9](=[O:28])[C:8]2=[O:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O>C(O)C>[NH2:20][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][C:14]=1[N+:17]([O-:19])=[O:18])[N:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:8](=[O:29])[C:9](=[O:28])[NH:10]2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22097075Ethyl N-(1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedion-6-yl)oxamate

Product 1

HCID 220970786-Amino-1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedioneYield 111.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

42 g (0.1 mol) of ethyl N-(1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedion-6-yl)oxamate were refluxed in a mixture of 11 of concentrated sulfuric acid and 500 ml of ethanol for 4 h. The precipitate was filtered off with suction to yield 34 g (100%) of the product. Melting point>250° C. (decomposition).

Workup

  1. filtrationThe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-48ccf87103c6452687d6d58471befaab
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

Loading…