HCID 58216632, compound → 3-Hydroxy-6-methoxy-3,4-dihydro-1,5-naphthyridin-2(1H)-one

HRID 1799572Notes

Reaction equation

HRID 1799572 reaction equation
[OH:1][CH:2]([CH2:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=1)[C:3](OCC)=[O:4].[H][H]>CO.[Pd]>[OH:1][CH:2]1[CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=2)[NH:15][C:3]1=[O:4]

Participants

5

Reactant 2

HCID 58216632HCID 58216632, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 534147233-Hydroxy-6-methoxy-3,4-dihydro-1,5-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A roundbottom flask was charged with a solution of ethyl 2-hydroxy-3-(6-methoxy-3-nitropyridin-2-yl)propanoate (37 mmol) in methanol (500 ml). To the mixture was added 10% palladium on carbon (3 g). The solution was shaken under 40 psi of hydrogen for 12 hours. The resulting solution was then allowed to react, with stirring, for 5 hours while the temperature was maintained at room temperature. The mixture was then filtered and the filtrate was diluted with 100 ml of water. Hydrochloric acid was added until the pH=5. The mixture was filtered and the filtrate was adjusted to pH=8 by the addition of sodium carbonate. The solids that formed were collected by filtration to afford the title compound.

Workup

  1. customto react
  2. filtrationThe mixture was then filtered
  3. additionthe filtrate was diluted with 100 ml of water
  4. additionHydrochloric acid was added until the pH=5
  5. filtrationThe mixture was filtered
  6. additionthe filtrate was adjusted to pH=8 by the addition of sodium carbonate
  7. customThe solids that formed
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-583e44e57fbc447db3003efe723ba0cf
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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