Hydroxyamine hydrochloride → 2-Hydroxy-3-methylbenzonitrile

HRID 450845Notes

Reaction equation

HRID 450845 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:12]O.C([O-])(=O)C.[Na+]>C(O)=O>[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:12]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5227773-Methylsalicylaldehyde

Product 1

HCID 143886552-Hydroxy-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-hydroxy-3-methyl-benzaldehyde (1.13 g, 8.29 mmol), hydroxylamine hydrochloride (0.69 g, 9.9 mmol) and sodium acetate (0.8 g, 9.9 mmol) in formic acid (20 ml) is heated at reflux over night. The solvent is evaporated under reduced pressure and the residue is partitioned between water and ethyl acetate. The organic phase is dried and evaporated to dryness. Chromatography yields the title compound. (CDCl3, 400 MHz): 7.32 (m, 2H); 6.89 (t, 1H); 5.65 (s, 1H); 2.23 (s, 3H).

Workup

  1. temperatureat reflux over night
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is partitioned between water and ethyl acetate
  4. customThe organic phase is dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f6324c01412641f18ecf6d64a9d16a72
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

Loading…