O-ethylhydroxylamine hydrochloride → HCID 136016119, compound

HRID 428804Notes

Reaction equation

HRID 428804 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=O)[C:18](=[N:20][OH:21])[CH3:19])=[CH:13][CH:12]=2)[CH3:9])=[CH:4][CH:3]=1.Cl.[CH2:24]([O:26][NH2:27])[CH3:25]>N1C=CC=CC=1>[CH2:24]([O:26][N:27]=[C:17]([C:14]1[CH:15]=[CH:16][C:11]([O:10][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH3:9])=[CH:12][CH:13]=1)[C:18](=[N:20][OH:21])[CH3:19])[CH3:25]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 73431884HCID 73431884, compound

Product 1

HCID 136016119HCID 136016119, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 29.0 g of 1-(4-(1-{4-chlorophenyl}-ethoxy)-phenyl)-1,2-propanedione-2-oxime and 9.4 g of O-ethylhydroxylamine hydrochloride in 150 ml of pyridine is boiled at reflux for 1 hour. After cooling, the reaction mixture is concentrated by evaporation in vacuo. The residue is dissolved in ethyl acetate; the organic phase is washed twice with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The crude product is stirred together with hexane; filtration is carried out and the filter residue is dried, yielding the title product having a melting point of 132-134° C.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated by evaporation in vacuo
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washthe organic phase is washed twice with water and once with saturated sodium chloride solution
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated by evaporation
  8. filtrationfiltration
  9. customthe filter residue is dried

Sources & evidence

ORD record
ord-2a6448ae8fc74b74be7d23386e100e1f
Source dataset
uspto-grants-2001_11
Patent number
US06313344B1

Reaction notes

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