Nitromethane → HCID 178526916, compound

HRID 542554Notes

Reaction equation

HRID 542554 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 2g (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-72d1064f513a4b0d9bb29cd3ea4f80fd
Source dataset
uspto-grants-1987_04
Patent number
US04658028

Reaction notes

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