Sodium Carbonate → N-Hydroxy-2-methoxy-benzamidine

HRID 1288262Notes

Reaction equation

HRID 1288262 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>O.C(O)C>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[C:14](=[N:2][OH:3])[NH2:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 810862-MethoxybenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 4652214N-Hydroxy-2-methoxy-benzamidineYield 30.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of hydroxylamine hydrochloride (245 g.) and sodium carbonate (170 g.) in water (2.6 l.) was added a solution of 2-methoxybenzonitrile (127.5 g.) in ethanol (1.25 l.), and the mixture refluxed with stirring for 1.5 hours. The solution was concentrated in vacuo to low bulk and the resultant oil crystallised on standing. The solid was filtered off, washed with water to remove inorganic salts, dried at 60° C., and recrystallised from benzene to give 2-methoxybenzamidoxime (49.2 g.), m.p. 117°-119° C. Further material (21.2 g., m.p. 119°-120° C.) was obtained by concentration of the recrystallisation mother liquor.

Workup

  1. temperaturethe mixture refluxed
  2. concentrationThe solution was concentrated in vacuo to low bulk
  3. customthe resultant oil crystallised
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customto remove inorganic salts
  7. customdried at 60° C.
  8. customrecrystallised from benzene

Sources & evidence

ORD record
ord-ab268711ae6f497ab9671897052f6e40
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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