Nitromethane → HCID 178526916, compound

HRID 2413975Notes

Reaction equation

HRID 2413975 reaction equation
O.[CH:2]([C:4]1[CH:13]=[N+:12]([O-:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]=1[O-:15])=[O:3].[N+:16]([CH3:19])([O-:18])=[O:17]>CO.C(N(CC)CC)C>[OH:3][CH:2]([C:4]1[CH:13]=[N+:12]([O-:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]=1[O-:15])[CH2:19][N+:16]([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 6375NitromethaneHCID 1785269452-Formylquinoxaline-1,4-dioxide hydrate

Product 1

HCID 178526916HCID 178526916, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 887MethanolSolvent

Procedure

2-Formylquinoxaline-1,4-dioxide hydrate 2 g (0.01 mole) was dissolved in 100 ml of warm methanol. Ten drops of triethylamine were added with stirring and 1.3 g of nitromethane was added incrementally. The heat source was removed and the reaction mixture was allowed to cool to room temperature. The methanol was removed by evaporation and the residue was recrystallized from water, 1 g/75 ml. There was obtained 2-(1-hydroxy-2-nitroethyl)quinoxaline-1,4-dioxide, m.p. 202°-204° C. with decomposition. This compound was dissolved in an excess of warm acetyl chloride. The mixture was heated to boiling for about 30 minutes, then allowed to cool. The solids which separated were isolated by filtration, rinsed with ether and dried. A sample was purified by recrystallization from a mixture of dimethylsulfoxide and methanol (1 g/5 ml/45 ml respectively). There was obtained 2-(1-acetoxy-2-nitroethyl)quinoxaline-1,4-dioxide, m.p. 201°-204° C. It analyzed as follows:

Workup

  1. customThe heat source was removed
  2. customThe methanol was removed by evaporation
  3. customthe residue was recrystallized from water, 1 g/75 ml

Sources & evidence

ORD record
ord-091e28b3f73e4edf8fda3d55ef595151
Source dataset
uspto-grants-1988_01
Patent number
US04720548

Reaction notes

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