7-(2,4-Dimethoxy-benzyl)-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester → 4-Hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

HRID 919789Notes

Reaction equation

HRID 919789 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:27])[N:10](CC3C=CC(OC)=CC=3OC)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4]>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:27])[NH:10][CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4]

Participants

3

Reactant 1

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

Product 1

HCID 682972414-Hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl esterYield 61.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-(2,4-dimethoxy-benzyl)-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (60 mg, 0.162 mmol) in TFA (3 mL) was refluxed for 16 h. Solvent was evaporated in vacuo, and the residue was partitioned between CH2Cl2 and saturated NaHCO3. The aqueous layer was extracted with 10% MeOH/CH2Cl2 until the layers were free of solid. The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to give 22 mg of the title compound as a pale brown solid. MS: (+) m/z 221.25 (M+1).

Workup

  1. customSolvent was evaporated in vacuo
  2. customthe residue was partitioned between CH2Cl2 and saturated NaHCO3
  3. extractionThe aqueous layer was extracted with 10% MeOH/CH2Cl2 until the layers
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-11a6545cbd004a70a2c30cbc9b28d158
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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