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Sodium Nitrate → Ethyl N-(1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedion-6-yl)oxamate

HRID 861486
Notes
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Reaction equation

HRID 861486 reaction equation
[CH:1]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([NH:17][C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:15]=3)[NH:10][C:9](=[O:25])[C:8]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:27]([O-])([O-:29])=[O:28].[Na+]>S(=O)(=O)(O)O>[CH:1]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([NH:17][C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]([N+:27]([O-:29])=[O:28])[CH:15]=3)[NH:10][C:9](=[O:25])[C:8]2=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 22097144Ethyl N-(1-cyclohexyl-2,3(1H,4H)-quinoxalinedion-6-yl)oxamate

Product 1

HCID 22097075Ethyl N-(1-cyclohexyl-7-nitro-2,3(1H,4H)-quinoxalinedion-6-yl)oxamateYield 93.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

48 g (0.133 mol) of ethyl N-(1-cyclohexyl-2,3(1H,4H)-quinoxalinedion-6-yl)oxamate were dissolved in 11 of concentrated sulfuric acid and, at 0° C., 11.35 g (0.133 mol) of sodium nitrate were added a little at a time. The mixture was stirred at 0° C. for a further 2 h and poured into a large quantity of ice. The precipitate was filtered off with suction to yield 50.1 g (93%) of the product.

Workup

  1. additionpoured into a large quantity of ice
  2. filtrationThe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-7e4c24da394c4efcb0f1513404fddf2d
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05714489

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes