HCID 58267711, compound → HCID 178466628, compound

HRID 1920720Notes

Reaction equation

HRID 1920720 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[C:10]([NH:13][CH3:14])=[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])[NH:13][CH3:14])[CH3:2]

Participants

4

Reactant 1

HCID 58267711HCID 58267711, compound

Product 1

HCID 178466628HCID 178466628, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.75 g [14.31 mmol] of 4-ethoxy-N-methyl-1,2-benzisoxazol-3-amine are hydrogenated in 30 ml of methanol and in the presence of 0.28 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 1.1 g of product as a grey solid; the purity is >95% according to 1H NMR.

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-56bb29ac268b42d4a99563e0f98cca6a
Source dataset
uspto-grants-2012_05
Patent number
US08173641B2

Reaction notes

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