Water → HCID 59403300, compound

HRID 1873865Notes

Reaction equation

HRID 1873865 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[C:10](/[N+:12]([O-:14])=[O:13])\[CH3:11].Cl.[CH3:16][O:17][NH2:18].C(N(CC)CC)C.O>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:18][O:17][CH3:16])[CH:10]([N+:12]([O-:14])=[O:13])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 2063266HCID 2063266, compound

Product 1

HCID 59403300HCID 59403300, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred yellow solution of the 2,4-dichloro-1-((E)-2-nitro-propenyl)-benzene (1.0 mmol, 0.232 g), in methanol (3 ml) under N2 was added at 0° C. O-methylhydroxylamine hydrochloride (2.0 mmol, 0.167 g) and triethylamine (3.0 mmol, 0.30 g). After stirring for 0.5 h at 50° C., the colourless liquid cooled to ambient temperature and water (20 ml) was added. The aqueous solution was extracted with dichloromethane (20 ml), the organic layers were combined, dried (MgSO4), filtered, and evaporated under reduced pressure to afford 0.23 g (82.4% of theory) of N-[1-(2,4-dichloro-phenyl)-2-nitro-propyl]-O-methyl-hydroxylamine in the form of liquid, as a mixture of diastereomeres.

Workup

  1. temperaturethe colourless liquid cooled to ambient temperature
  2. extractionThe aqueous solution was extracted with dichloromethane (20 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e49f27e3dc004eda80b8a42ff7c4c6fc
Source dataset
uspto-grants-2012_11
Patent number
US08304444B2

Reaction notes

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