Nitromethane → HCID 178526916, compound

HRID 542252Notes

Reaction equation

HRID 542252 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-(2-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-d77896bdaf4b435bb96d1f8df40474e8
Source dataset
uspto-grants-1987_04
Patent number
US04656276

Reaction notes

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