Hydroxyamine hydrochloride → 2-Hydroxy-3-methylbenzonitrile

HRID 636709Notes

Reaction equation

HRID 636709 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.[Na+]>C(O)=O>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:10])[C:2]=1[OH:1])#[N:12]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5227773-MethylsalicylaldehydeHCID 2723810Sodium Formate

Product 1

HCID 143886552-Hydroxy-3-methylbenzonitrileYield 82.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-hydroxy-3-methylbenzaldehyde (18.6 g), hydroxylamine hydrochloride (14.2 g) and sodium formate (19.2 g) in formic acid (200 mL) was heated at reflux for 18 h, then cooled and partitioned between DEE/water. The organic layer was washed with water, saturated aqueous sodium bicarbonate and brine, then dried over sodium sulfate and concentrated in vacuo to afford a solid. Recrystallization from diethyl ether/petroleum ether afforded the title compound as colorless crystals (15.0 g).

Workup

  1. temperatureat reflux for 18 h
  2. temperaturecooled
  3. custompartitioned between DEE/water
  4. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford a solid
  8. customRecrystallization from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-d376e8cc523a42cb886660f02a90b26a
Source dataset
uspto-grants-2001_02
Patent number
US06194454B1

Reaction notes

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