Water → N-(4-(4-Aminonaphthalen-1-yloxy)pyridin-2-yl)-2-methoxyacetamide

HRID 2069113Notes

Reaction equation

HRID 2069113 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N+:24]([O-])=O)=[CH:16][CH:15]=2)[CH:10]=[CH:9][N:8]=1)=[O:5].O>CN(C=O)C.[Pd]>[NH2:24][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH:12]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 962WaterHCID 674524762-Methoxy-N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)acetamide

Product 1

HCID 66718180N-(4-(4-Aminonaphthalen-1-yloxy)pyridin-2-yl)-2-methoxyacetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methoxy-N-(4-(4-nitronaphthalen-1-yloxy)pyridin-2-yl)acetamide (50.0 g, 142 mmol) in DMF (500 mL) under nitrogen was added palladium on carbon (10% w/w Pd/C, 5.0 g, 14.15 mmol) and the mixture was purged with hydrogen and maintained under a slight positive hydrogen atmosphere for 48 hr. The catalyst was removed by filtration through celite and the pad washed with DMF (2×100 mL) and then DCM (100 mL). The solvents were removed in vacuo to afford a dark brown residue which was treated with water (150 mL) and the mixture evaporated. Toluene (100 mL) was added and evaporated to remove residual water. After drying overnight under vacuum, the material was triturated from diethyl ether (250 mL) to give the title compound, Intermediate B1, as a green solid (43.3 g, 85%): m/z 324 (M+H)+ (ES+).

Workup

  1. customthe mixture was purged with hydrogen
  2. temperaturemaintained under a slight positive hydrogen atmosphere for 48 hr
  3. customThe catalyst was removed by filtration through celite
  4. washthe pad washed with DMF (2×100 mL)
  5. customThe solvents were removed in vacuo
  6. customto afford a dark brown residue which
  7. customthe mixture evaporated
  8. additionToluene (100 mL) was added
  9. customevaporated
  10. customto remove residual water
  11. customAfter drying overnight under vacuum
  12. customthe material was triturated from diethyl ether (250 mL)

Sources & evidence

ORD record
ord-5c25203ae55e4d77bac68aec664728e2
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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