Sulfuric acid magnesium salt (1:1) → 4-Hydroxy-3-iodobenzonitrile

HRID 1359593

Reaction equation

HRID 1359593 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[I:10].Cl.[NH2:12]O.S([O-])([O-])(=O)=O.[Mg+2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:12])=[CH:4][C:3]=1[I:10]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 443297Hydroxyamine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 9688814-Hydroxy-3-iodobenzaldehyde

Product 1

HCID 109558154-Hydroxy-3-iodobenzonitrileYield 84.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 4-hydroxy-3-iodo-benzaldehyde (7.9 g, 31.8 mmol) (prepared by the method of Barnes at al.; J. Chem. Soc., 1950, 2824) in xylene (120 mL) was added hydroxylamine hydrochloride (2.34 g, 33.4 mmol), magnesium sulphate (12.7 g) and p-toluene sulphonic acid monohydrate (1.27 g, 6.4 mmol). The resulting mixture was heated to reflux and stirred at this temperature for 90 min. The reaction mixture was then allowed to cool to room temperature and filtered. The solid was washed with ethyl acetate then the combined filtrates concentrated. The residue was purified by flash chromatography (eluting with 30% ethyl acetate in hexanes) to give 6.57 g of the title compound. 1H NMR (CDCl3) d 6.1 (bs, 1H), 7.05 (d, J=8 Hz, 1H), 7.55 (dd, J=8, 1 Hz, 1H), 7.99 (d, J=1 Hz, 1H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. washThe solid was washed with ethyl acetate
  5. concentrationthe combined filtrates concentrated
  6. customThe residue was purified by flash chromatography (eluting with 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-74c90156d63d4ed29a160e58081c1adf
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Linked notes

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