7-Chloro-1,8-naphthyridin-2-amine → 7-methoxy-1,8-Naphthyridin-2-amine

HRID 908

Reaction equation

HRID 908 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]=1

Participants

4

Reactant 2

HCID 851997-Chloro-1,8-naphthyridin-2-amineHCID 10942334Sodium Methoxide

Product 1

HCID 217930277-methoxy-1,8-Naphthyridin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. temperatureto cool
  2. filtrationfiltered through Celite
  3. concentrationconcentrated in vacuo
  4. 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

Linked notes

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