Potassium Hydroxide → HCID 178489516, compound

HRID 1616557Notes

Reaction equation

HRID 1616557 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-45a64b7b170e4854b6b06205052a12b4
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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