Sodium Hydroxide → 2-(Methylamino)-1,8-naphthyridine-3-carboxylic acid
Reaction equation
[CH3:1][NH:2][C:3]1[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[OH-].[Na+]>CCO>[CH3:1][NH: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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Ethyl 2-(methylamino)-1,8-naphthyridine-3-carboxylate (58 mg, 0.25 mmol) was dissolved in EtOH. NaOH (0.75 ml, 1M aqueous solution) was added to the solution and the mixture stirred at 40° C. for 5.0 h. The organic solvent was removed under vacuo. 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 50.0 mg (quant) of the title compound.
Workup
- customThe organic solvent was removed under vacuo
- additionThe remaining aqueous residue was treated with HCl (1M aqueous solution) until slightly acidic and the product
- extractionextracted with EtOAc
- dry with materialThe combined organic phases were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-88513ff0f3f642b6af055c6c60df398f
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415333B2
Reaction notes
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