tert-Butyl 3-nitro-2-oxo-1(2H)-pyridineacetate → 3-Amino-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 1251361Notes

Reaction equation

HRID 1251361 reaction equation
[N+:1]([C:4]1[C:5](=[O:18])[N:6]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>[Pd].CO>[C:14]([O:13][C:11](=[O:12])[CH2:10][N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([NH2:1])[C:5]1=[O:18])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 18989321tert-Butyl 3-nitro-2-oxo-1(2H)-pyridineacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 44562653-Amino-1-(tert-butoxycarbonylmethyl)-2-pyridinoneYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The compound of Example 137 (54 g, 0.213 mole) and 880 ml of methanol and 5 g of 10% palladium on carbon were stirred under 1 Atm of hydrogen for 24 hours. The reaction mixture was filtered and the carbon was washed with 200 mL of dichloromethane. The organic layer was evaporated to yield 47.08 g (98.5 %) of the title compound as a brown solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe carbon was washed with 200 mL of dichloromethane
  3. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-1dbb1cb47ba34d7d92e52f61acd5b6de
Source dataset
uspto-grants-2002_01
Patent number
US06342504B1

Reaction notes

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