2-Hydroxy-5-methoxybenzaldehyde → 2-Hydroxy-5-methoxybenzonitrile

HRID 2224653Notes

Reaction equation

HRID 2224653 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:13]O.C([O-])=O.[Na+]>C(O)=O>[C:4]([C:3]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:2]=1[OH:1])#[N:13]

Participants

5

Reactant 3

HCID 956952-Hydroxy-5-methoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium Formate

Product 1

HCID 70225292-Hydroxy-5-methoxybenzonitrileYield 51.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 2-hydroxy-5-methoxybenzaldehyde (4.00 g) in formic acid (30 ml) were added hydroxylamine hydrochloride (2.01 g) and sodium formate (3.22 g) at room temperature and the mixture was refluxed for 2 hours. The reaction mixture was concentrated. the residue was diluted with water and was extracted with t-butyl methyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with a mixture of t-butyl methyl ether and hexane to give the title compound (2.02 g) having the following physical data.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with water
  4. extractionwas extracted with t-butyl methyl ether
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. washThe residue was washed with a mixture of t-butyl methyl ether and hexane

Sources & evidence

ORD record
ord-66ded5426d0e41e78033e82cf97b1989
Source dataset
uspto-grants-2008_05
Patent number
US07378428B2

Reaction notes

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