O-Allylhydroxylamine → 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde-O-allyl oxime

HRID 357285Notes

Reaction equation

HRID 357285 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O.[CH2:19]([O:22][NH2:23])[CH:20]=[CH2:21]>C(OCC)(=O)C>[CH2:19]([O:22][N:23]=[CH:13][C:12]1[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=1[NH:10][C:3]1[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[Cl:1])[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 420841O-AllylhydroxylamineHCID 150273772-[(2,6-Dichloro-3-methylphenyl)amino]benzaldehyde

Product 1

HCID 867533572-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde-O-allyl oximeYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution in 3:1 ethanol-pyridine of 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde, prepared as in Example 1, steps 1-2, and O-allyl hydroxylamine(1.3 eq) was heated at reflux for 2 days. The reaction mixture was poured into ethyl acetate and the mixture was extracted with 10% aqueous HCl. Chromatography on silica gel (20% CH2Cl2 /hexanes) gave 2-[(2,6-dichloro-3-methylphenyl)amino]benzaldehyde-O-allyl oxime (1.13 g, 94%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. extractionthe mixture was extracted with 10% aqueous HCl

Sources & evidence

ORD record
ord-e3fa647ebc19415aaf4056e716c3f77f
Source dataset
uspto-grants-1998_11
Patent number
US05840758

Reaction notes

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