Potassium Hydroxide → HCID 178489516, compound

HRID 1039171Notes

Reaction equation

HRID 1039171 reaction equation
[OH-:1].[K+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].Cl.[NH2:14]O>C(O)C>[OH:1][NH:8][C:7](=[NH:14])[C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[O:4][CH3:3]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 810862-MethoxybenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178489516HCID 178489516, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add potassium hydroxide (30.3 g, 225 mmol) to a solution of 2-methoxybenzonitrile (25.0 g, 187 mmol) and hydroxylamine hydrochloride (15.77 g, 225 mmol) in ethanol (500 mL) at room temperature under nitrogen and heat the mixture at reflux for 12 hours. Remove the solvent under reduced pressure, triturate the residue with ethyl acetate/hexanes (1:9, 300 mL) and collect by vacuum filtration to provide N-hydroxy-2-methoxybenzamidine (24.0 g, 91%).

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux for 12 hours
  3. customRemove the solvent under reduced pressure
  4. customtriturate the residue with ethyl acetate/hexanes (1:9, 300 mL)
  5. filtrationcollect by vacuum filtration

Sources & evidence

ORD record
ord-7238ecd630ad47eea5ad83e7fa4eabd7
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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