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

HRID 332602Notes

Reaction equation

HRID 332602 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-459dab117c04469a84043b35e44f601a
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

Loading…