Methanol → 4-[(7-Oxo-5,6,7,8-tetrahydro[1,8]naphthyridin-4-yl)oxy]aniline

HRID 853316Notes

Reaction equation

HRID 853316 reaction equation
[NH2:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10](OCC)=[O:11])=[C:6]([O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[CH:5]=[CH:4][N:3]=1.CO.[H][H]>[C].[Pd].O1CCCC1>[O:11]=[C:10]1[NH:1][C:2]2[N:3]=[CH:4][CH:5]=[C:6]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[C:7]=2[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 887MethanolHCID 58931221Ethyl(E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 589310804-[(7-Oxo-5,6,7,8-tetrahydro[1,8]naphthyridin-4-yl)oxy]anilineYield 16.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl(E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoate (330 mg), palladium-carbon (10%, aqueous, 100 mg), methanol (5 ml) and tetrahydrofuran (5 ml) were stirred overnight at under a hydrogen atomsphere at 1 atmosphere. The palladium-carbon was filtered off, the filtrate was distilled off under reduced pressure, and then the residue was purified by silica gel column chromatography (ethyl acetate, followed by ethyl acetate:methanol=5:1) to obtain 43 mg of a white solid.

Workup

  1. filtrationThe palladium-carbon was filtered off
  2. distillationthe filtrate was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate, followed by ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-0f3bae5539d84f929ba4e20ac74ad7fe
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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