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

HRID 1410778Notes

Reaction equation

HRID 1410778 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-c1f5233a93ed46fcadb0ab8d5e54b058
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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