Reaction #11970

Reaction equation

compound

Methyl 4-bromomethyl-1-naphthalene Carboxylate

potassium carbonate

2-aminopyridine

→

title compound

Yield 9.5%

4-(2-pyridyl)aminomethylnaphthalene-1-carboxylic acid

Yield 9.5%

Solvents

DMF

Conditions

Workup

1. 1
   OtherAfter the reaction
2. 2
   Otherthe solvent was removed by distillation
3. 3
   workup.DISSOLUTIONthe residue was dissolved in chloroform
4. 4
   WashThe organic layer was washed with 1 mol/l aqueous solution of hydrochloric acid and saturated brine
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   OtherThen, the solvent was removed by distillation
7. 7
   workup.DISSOLUTIONThe residue was dissolved in DMF (44 ml)
8. 8
   workup.ADDITION(1.58 ml) and di-t-butyldicarbonate (2.60 ml) were added
9. 9
   workup.STIRRINGthe mixture was stirred for 6 hours at room temperature
10. 10
    OtherAfter the reaction
11. 11
    Otherthe solvent was removed by distillation
12. 12
    workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
13. 13
    WashThe solution was washed with 0.5 mol/l aqueous solution of hydrochloric acid and saturated brine
14. 14
    Dryingdried over anhydrous sodium sulfate
15. 15
    OtherThe solvent was removed by distillation
16. 16
    workup.DISSOLUTIONThe residue was dissolved in methanol (6 ml)
17. 17
    workup.ADDITION1 mol/l aqueous solution of sodium hydroxide (6 ml) was added
18. 18
    OtherAfter the reaction for one day
19. 19
    Concentrationthe reaction solution was concentrated
20. 20
    workup.DISSOLUTIONThe residue was dissolved again in methanol and neutralized with ion-exchange resin CG50
21. 21
    OtherThe resin was removed by filtration
22. 22
    ConcentrationThe filtrate was concentrated
23. 23
    OtherThe residue was purified by silica gel column chromatography (15 g, chloroform/methanol=5/1)

Procedure

The compound obtained in Example 17-2 (1.6728 g) was dissolved in DMF (33 ml). After the addition of potassium carbonate (1.66 g) and 2-aminopyridine (0.68 g), the mixture was stirred for 15 hours at room temperature. After the reaction, the solvent was removed by distillation and the residue was dissolved in chloroform. The organic layer was washed with 1 mol/l aqueous solution of hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. Then, the solvent was removed by distillation. The residue was dissolved in DMF (44 ml). Triethylamine. (1.58 ml) and di-t-butyldicarbonate (2.60 ml) were added and the mixture was stirred for 6 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved in ethyl acetate. The solution was washed with 0.5 mol/l aqueous solution of hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was dissolved in methanol (6 ml), and 1 mol/l aqueous solution of sodium hydroxide (6 ml) was added. After the reaction for one day, the reaction solution was concentrated. The residue was dissolved again in methanol and neutralized with ion-exchange resin CG50. The resin was removed by filtration. The filtrate was concentrated. The residue was purified by silica gel column chromatography (15 g, chloroform/methanol=5/1) to obtain the title compound (159 mg) as a colorless viscous liquid.

Source