Sodium Hydroxide → 2-Methoxy-1,8-naphthyridine-3-carboxylic acid

HRID 1961446Notes

Reaction equation

HRID 1961446 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66633977Methyl 2-methoxy-1,8-naphthyridine-3-carboxylate

Product 1

HCID 666336762-Methoxy-1,8-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-methoxy-1,8-naphthyridine-3-carboxylate (87.0 mg, 0.40 mmol) was dissolved in MeOH. NaOH (1.2 ml, 1M aqueous solution) was added to the solution and the mixture stirred at room temperature for 18 h. The organic solvent was removed under reduced pressure. The remaining aqueous residue was treated with HCl (1M aqueous solution) until slightly acidic and the product extracted with EtOAc. The combined organic phases were dried over MgSO4, filtered and concentrated yielding 2-methoxy-1,8-naphthyridine-3-carboxylic acid which was coupled without further purification to 3-(trifluoromethyl)benzylamine using the general amide coupling procedure. The crude product was purified by flash chromatography, CH2Cl2/MeOH 96:4, yielding 124 mg (86%) of the title compound.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. additionThe remaining aqueous residue was treated with HCl (1M aqueous solution) until slightly acidic and the product
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-51dc4dee2ada4905aef11a497fe6e968
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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