4-Cyanobenzaldehyde → 4-Cyanobenzaldehyde oxime

HRID 708942Notes

Reaction equation

HRID 708942 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.Cl.[NH2:12][OH:13].C([O-])(=O)C.[Na+]>CO.CCOCC>[OH:13][N:12]=[CH:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 52147424-Cyanobenzaldehyde oximeYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

The compound was prepared according to Biasotti et al. Bioorg. Med. Chem. 2003, 11, 2247. A suspension of 4-formylbenzonitrile (500 mg, 3.81 mmol, 1.00 eq), hydroxylamine hydrochloride (290 mg, 4.19 mmol, 1.10 eq), and sodium acetate (1.56 g, 19.05 mmol, 5.00 eq) in MeOH (50 mL) was heated at 70° C. for 4 h before concentration to dryness. The residue was then slurried in Et2O, filtered, and concentrated to afford the desired intermediate (496 mg, 3.39 mmol, 89%).

Workup

  1. customThe compound was prepared
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-10dc130bb0f042a48f91fa78a484d515
Source dataset
uspto-grants-2015_11
Patent number
US09179681B2

Reaction notes

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