O-Methylhydroxylamine → HCID 86742748, compound

HRID 1382228Notes

Reaction equation

HRID 1382228 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:20])[CH2:10][CH2:11][NH:12][C:13](SC)=[CH:14][N+:15]([O-:17])=[O:16])=[CH:4][N:3]=1.[CH3:21][O:22][NH2:23]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:20])[CH2:10][CH2:11][NH:12][C:13]([NH:23][O:22][CH3:21])=[CH:14][N+:15]([O-:17])=[O:16])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4113O-MethylhydroxylamineHCID 72727591HCID 72727591, compound

Product 1

HCID 86742748HCID 86742748, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.95 g of the compound synthesized in Example 1 above in 30 ml of ethanol was added O-methylhydroxylamine (0.16 g), and the mixture was heated under reflux for 1 hour. The ethanol was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the desired N-(2-chloro-5-pyridylmethyl)-N-methyl-N'-(1-methoxyamino-2-nitrovinyl)ethylenediamine (0.6 g) having an nD20 of 1.5466.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe ethanol was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cfa43bfec8ad49f2b977cc968c29a6b2
Source dataset
uspto-grants-1989_02
Patent number
US04806553

Reaction notes

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