7-Chloro-1,8-naphthyridin-2-amine → 7-methoxy-1,8-Naphthyridin-2-amine
Reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([NH2:12])=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([NH2:12])=[CH:7][CH:8]=2)[N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-chloro-7-amino-1,8-napthyridine (Newkome, G. R. et al, J. Org. Chem., 1981, 46, 833-39) (180 mg, 1 mmol) and a methanolic solution of sodium methoxide (458 μL, 25 wt. %) in methyl alcohol (2 mL) was heated at 50° C. for 19 hours. The reaction mixture was allowed to cool, filtered through Celite using dichloromethane, concentrated in vacuo and the residue purified on Silica gel (1:9:0.2 methyl alcohol/dichloromethane/ammonium hydroxide) to afford 2-methoxy-7-amino-1,8-naphthyridine as a pale yellow solid.
Workup
- temperatureto cool
- filtrationfiltered through Celite
- concentrationconcentrated in vacuo
- customthe residue purified on Silica gel (1:9:0.2 methyl alcohol/dichloromethane/ammonium hydroxide)
Sources & evidence
- ORD record
- ord-5cd86490cc5f416d8215674f1fbf73d6
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05723462
Reaction notes
Loading…