1-Chloro-2,4-Dinitrobenzene → N-Methoxy-2,4-dinitroaniline

HRID 1356628Notes

Reaction equation

HRID 1356628 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1Cl)([O-:3])=[O:2].Cl.[O:15]([NH2:17])[CH3:16].C(N(CC)CC)C>C(#N)C>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:17][O:15][CH3:16])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 12102671N-Methoxy-2,4-dinitroanilineYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,4-Dinitrochlorobenzene (4.05 g (20.0 mmol)) and methoxylamine hydrochloride (2.00 g (23.9 mmol)) were dissolved in 15 ml of acetonitrile. To this mixture, under ice cooling and with stirring, triethylamine (7.00 ml (50.2 mmol)) was added. After being stirred for 24 hours at room temperature, the resulting black solution was concentrated under reduced pressure.Water and dilute hydrochloric acid were added to the residue and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was then subjected to silica gel column chromatography with ethyl acetate-hexane (1:5) as eluent, to give 2.26 g (53%) of N-(2,4-dinitrophenyl)-O-methylhydroxylamine as yellow crystals.

Workup

  1. stirringAfter being stirred for 24 hours at room temperature
  2. concentrationthe resulting black solution was concentrated under reduced pressure
  3. additionWater and dilute hydrochloric acid were added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d18251b79264c4ca6c30c556313b857
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

Loading…