4-Ethoxybenzo[d]isoxazol-3-amine → 2-Ethoxy-6-hydroxybenzenecarboximidamide

HRID 1920719Notes

Reaction equation

HRID 1920719 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[C:10]([NH2:13])=[N:11][O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:12])[C:9]=1[C:10](=[NH:11])[NH2:13])[CH3:2]

Participants

4

Reactant 1

HCID 552785404-Ethoxybenzo[d]isoxazol-3-amine

Product 1

HCID 1360739132-Ethoxy-6-hydroxybenzenecarboximidamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.65 g [20.48 mmol] of 4-ethoxy-3-amino-1,2-benzisoxazole are hydrogenated in 40 ml of methanol and in the presence of 0.39 g of palladium (loading: 10, support: activated carbon) at room temperature and pressure 1 bar for 16 hours, analogously to the method from WO 2007/030582. The reaction mixture is filtered through silica gel, and rinsed through repeatedly with methanol. The combined filtrates are concentrated under reduced pressure. This leaves 1.9 g of product as a beige solid; the purity according to LC-MS is 100%.

Workup

  1. filtrationThe reaction mixture is filtered through silica gel
  2. washrinsed through repeatedly with methanol
  3. concentrationThe combined filtrates are concentrated under reduced pressure

Sources & evidence

ORD record
ord-9c2f572a4b5c46f78187db465ce03f23
Source dataset
uspto-grants-2012_05
Patent number
US08173641B2

Reaction notes

Loading…