O-((2E)-3-Chloro-2-propen-1-yl)hydroxylamine → HCID 178458080, compound

HRID 1606868Notes

Reaction equation

HRID 1606868 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:12][C:11](=[O:13])[CH:10]([C:14](=O)[CH2:15][CH3:16])[C:9](=[O:18])[CH2:8]2)=[CH:5][C:4]([CH3:19])=[N:3]1.[Cl:20]/[CH:21]=[CH:22]/[CH2:23][O:24][NH2:25]>CO>[Cl:20][CH:21]=[CH:22][CH2:23][O:24]/[N:25]=[C:14](/[CH:10]1[C:11](=[O:13])[CH2:12][CH:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([CH3:19])[CH:5]=2)[CH2:8][C:9]1=[O:18])\[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 158058O-((2E)-3-Chloro-2-propen-1-yl)hydroxylamineHCID 145362605-(1,3-dimethyl-1H-pyrazol-5-yl)-2-propionylcyclohexane-1,3-dione

Product 1

HCID 178458080HCID 178458080, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml of a solution of 5.60 g (21.3 mmols) of 5-(1,3-dimethyl-1H-pyrazol-5-yl)-2-propionylcyclohexane-1,3-dione in methanol was added 57 ml (21.7 mmols) of 0.38 mol ethanolic solution of (E)-3-chloro-2-propenyloxyamine. The mixture was reacted for 10 hours with stirring. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 6.84 g of the product.

Workup

  1. customThe mixture was reacted for 10 hours
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-517fdeb7e1764c90831793729aa18792
Source dataset
uspto-grants-1989_09
Patent number
US04863504

Reaction notes

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