4-Hydroxy-3-methoxybenzonitrile → 4-Hydroxy-3-methoxybenzenecarboximidamide hydrochloride

HRID 517333Notes

Reaction equation

HRID 517333 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[C:6]#[N:7].[ClH:12].O1CCOCC1.C(=O)([O-])[O-].[NH4+:23].[NH4+]>C(O)C>[ClH:12].[C:6]([C:5]1[CH:8]=[CH:9][C:10]([OH:11])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[NH:23])[NH2:7]

Participants

5

Reactant 3

HCID 781354-Hydroxy-3-methoxybenzonitrileHCID 517111Ammonium CarbonateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 1360432854-Hydroxy-3-methoxybenzenecarboximidamide hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3-methoxy-4-hydroxybenzonitrile (2.0 g, 13.4 mmol) were added ethanol (3 mL) and 4N hydrochloric acid/1,4-dioxane (27 mL), and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in ethanol (50 mL). Ammonium carbonate (6.4 g, 67 mmol) was added, and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, water was added and the mixture was freeze-dried to give the title compound (1.82 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol (50 mL)
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe solvent was evaporated under reduced pressure, water
  5. additionwas added
  6. customthe mixture was freeze-dried

Sources & evidence

ORD record
ord-ca40c8af68e04477a013b2013ab94369
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

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