4-Cyanobenzaldehyde → 4-Cyanobenzaldehyde oxime

HRID 2394375Notes

Reaction equation

HRID 2394375 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:12][OH:13]>N1C=CC=CC=1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:12][OH:13])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 660424-Cyanobenzaldehyde2×HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 52147424-Cyanobenzaldehyde oximeYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

This material was prepared from 4-cyanobenzaldehyde according to Kawase and Kikugawa (J. Chem. Soc., Perkin Trans I 1979, 643). To a solution of 4-cyanobenzaldehyde (1.31 g, 10 mmol) in 1:1EtOH:pyridine (10 mL) was added hydroxylamine hydrochloride (0.70 g, 10 mmol). The resulting solution was stirred at room temperature for 18 h and was concentrated in vacuo to one-half volume. To this solution was added ice water, causing the product to crystallize from solution. Recrystallization from EtOH--water followed by drying over P2O5 afforded 1.46 g (100%) of the desired oxime; mp: 167.8-169.4° C.

Workup

  1. concentrationwas concentrated in vacuo to one-half volume
  2. additionTo this solution was added ice water
  3. customto crystallize from solution
  4. customRecrystallization from EtOH
  5. dry with materialby drying over P2O5

Sources & evidence

ORD record
ord-3958b1d1f8034a33932db5e23b053769
Source dataset
uspto-grants-1998_09
Patent number
US05811441

Reaction notes

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