O-Methylhydroxylamine hydrochloride → HCID 178449944, compound

HRID 529878Notes

Reaction equation

HRID 529878 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH:17][CH:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[C:9]([C:12](=O)[CH2:13][CH2:14][CH3:15])[C:10]#[N:11].Cl.[O:24]([NH2:26])[CH3:25]>C(O)C.S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH:17][CH:18]([CH:20]([CH3:22])[CH3:21])[CH3:19])=[C:9]([C:12](=[N:26][O:24][CH3:25])[CH2:13][CH2:14][CH3:15])[C:10]#[N:11]

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 69671260HCID 69671260, compound

Product 1

HCID 178449944HCID 178449944, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-{(2-chlorophenyl)[(3-methylbutan-2-yl)amino]methylene}-3-oxohexanenitrile (0.300 g, 0.919 mmol, 1 eq.) in ethanol (6 ml) were added methoxylamine hydrochloride (0.314 g, 3.67 mmol, 4 eq.) followed by 2 drops of concentrated sulfuric acid. The reaction was microwaved (150° C., 22000 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was triturated in ethyl acetate and washed with sat. aq. solution of NaCl. After drying over MgSO4 and concentration under vacuum, the residual oil was subjected to preparative HPLC to give 2-{(2-chlorophenyl)[(3-methylbutan-2-yl)amino]methylene}-3-(methoxyimino)hexanenitrile (0.163 g, 49% yield).

Workup

  1. customThe reaction was microwaved
  2. custom(150° C., 22000 s, fixed hold, high absorption)
  3. customthe solvent evaporated
  4. customThe residual oil was triturated in ethyl acetate
  5. washwashed with sat. aq. solution of NaCl
  6. dry with materialAfter drying over MgSO4 and concentration under vacuum

Sources & evidence

ORD record
ord-c8f24266dcee4947b05b3b1e49ae0161
Source dataset
uspto-grants-2016_05
Patent number
US09351489B2

Reaction notes

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