Hydroxyamine hydrochloride → 3-Hydroxy-4-(hydroxyimino-methyl)-benzonitrile

HRID 1247348Notes

Reaction equation

HRID 1247348 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[OH:11])=O.C([O-])(=O)C.[Na+].Cl.[NH2:18][OH:19]>C(O)C>[OH:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[CH:1]=[N:18][OH:19])[C:7]#[N:8]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 128136484-Formyl-3-hydroxybenzonitrile

Product 1

HCID 1363363533-Hydroxy-4-(hydroxyimino-methyl)-benzonitrileYield 61.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-formyl-3-hydroxy-benzonitrile (CAS 84102-89-6) (6.90 g) in dry ethanol (165 ml) was added sodium acetate (4.23 g) and hydroxylamine hydrochloride (3.58 g). The mixture was stirred at rt for 1 h. The solvent was evaporated and the product was purified by flash chromatography (cyclohexane/EtOAc 8:2=>1:1) to give 3-hydroxy-4-(hydroxyimino-methyl)-benzonitrile (4.70 g). Light yellow solid. MS 162.0 ([M]+)

Workup

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

Sources & evidence

ORD record
ord-9e3cb85d367a449f996f52c68e5be7da
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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