Hydroxyamine hydrochloride → 4-(Hydroxyimino-methyl)-3-phenoxy-benzonitrile

HRID 1247345Notes

Reaction equation

HRID 1247345 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.C([O-])(=O)C.[Na+].Cl.[NH2:24][OH:25]>C(O)C>[OH:25][N:24]=[CH:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 219054244-Cyano-2-phenoxybenzaldehyde

Product 1

HCID 865930434-(Hydroxyimino-methyl)-3-phenoxy-benzonitrileYield 60.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-formyl-3-phenoxy-benzonitrile (2.21 g) in dry ethanol (45 ml) was added sodium acetate (0.894 g) and hydroxylamine hydrochloride (0.757 g). The mixture was stirred at rt for 4.5 h. The solvent was evaporated and the product was purified by flash chromatography (cyclohexane/EtOAc 8:2=>3:7) to give 4-(hydroxyimino-methyl)-3-phenoxy-benzonitrile (1.42 g). Light yellow solid. MS 238.1 ([M]+)

Workup

  1. customThe solvent was evaporated
  2. customthe product was purified by flash chromatography (cyclohexane/EtOAc 8:2=>3:7)

Sources & evidence

ORD record
ord-b1c3410b43504bfd829b5abcd5e5e57f
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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