Ethanol → 7-(2,4-Dimethoxy-benzyl)-4-hydroxy-8-oxo-5,6,7,8-tetrahydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

HRID 919775Notes

Reaction equation

HRID 919775 reaction equation
CCO.[CH3:4][O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:12](=[O:30])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[O:28][CH3:29])[CH:14]=[CH:15][C:16]=2[C:17]=1[OH:18])=[O:7]>[Pd].CCOC(C)=O.C1COCC1>[CH3:4][O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:12](=[O:30])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[O:28][CH3:29])[CH2:14][CH2:15][C:16]=2[C:17]=1[OH:18])=[O:7]

Participants

5

Reactant 2

HCID 702EthanolHCID 682972407-(2,4-Dimethoxy-benzyl)-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Product 1

HCID 682975387-(2,4-Dimethoxy-benzyl)-4-hydroxy-8-oxo-5,6,7,8-tetrahydro-[2,7]naphthyridine-3-carboxylic acid methyl esterYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

A round bottom flask was charged with 10% palladium on carbon (50 mg) and EtOH (5 mL). 7-(2,4-Dimethoxy-benzyl)-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (20 mg, 0.054 mmol) dissolved in EtOAc/THF (10 mL, 1:1) was added, and the mixture was stirred under H2 atmosphere (1 atm) for 16 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (5-80% EtOAc/hexanes+2% AcOH) to give 15 mg of the title compound. MS: (+) m/z 373.33 (M+H).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (5-80% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-e3eb0dba166b42fb9f3a9eda794116a1
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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