2-Hydroxy-4-Methoxybenzaldehyde → 2-Hydroxy-4-methoxybenzonitrile

HRID 1839353Notes

Reaction equation

HRID 1839353 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:13]O.C([O-])=O.[Na+]>C(O)=O>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:13]

Participants

5

Reactant 3

HCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium Formate

Product 1

HCID 114236802-Hydroxy-4-methoxybenzonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2-Hydroxy-4-methoxybenzaldehyde (55 g; 0.36 mol), hydroxylamine hydrochloride (30 g; 0.43 mol) and sodium formate (34 g; 0.5 mol) were refluxed in formic acid (200 ml; 98-100%) for 1.25 h. The solution was then rapidly chilled in an ice bath, with stirring over 30 min. The resulting precipitate was separated by filtration and washed well with water. Following drying, in a desicator under vacuum, the title compound was obtained (45 g; 0.3 mol; 84% yield) as a brick-red solid, mp 169-171° C., rf (EtOAc) 0.43.

Workup

  1. temperatureThe solution was then rapidly chilled in an ice bath
  2. customThe resulting precipitate was separated by filtration
  3. washwashed well with water
  4. customFollowing drying, in a desicator under vacuum

Sources & evidence

ORD record
ord-3cf8431ea5ee458290dcac1451857622
Source dataset
uspto-grants-2004_01
Patent number
US06677372B2

Reaction notes

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