Sodium Methoxide → 7-Methoxy-5-methyl-1,8-naphthyridin-2-amine

HRID 903873Notes

Reaction equation

HRID 903873 reaction equation
C([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[N:8][C:9](Cl)=[CH:10][C:11]=2[CH3:15])[N:6]=1)(=O)C.[CH3:17][O-:18].[Na+]>CO>[NH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[N:8][C:9]([O:18][CH3:17])=[CH:10][C:11]=2[CH3:15])[N:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 11345372AGN-PC-0078IQ

Product 1

HCID 147517137-Methoxy-5-methyl-1,8-naphthyridin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-acetamido-5-methyl-7-chloro-1,8-naphthyridine (23.5 g., 0.10 mole) in 250 ml. of methanol is added sodium methoxide (16.2 g., 0.30 mole). The resulting solution is stirred at reflux under nitrogen atmosphere for 18 hours. The methanol is removed in vacuo and the residue is taken up in chloroform (250 ml.) and water (100 ml.). The chloroform layer is separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue is recrystallized from ethanol to yield 2-amino-5-methyl-7-methoxy-1,8-naphthyridine melting at 233°-236° C.

Workup

  1. temperatureat reflux under nitrogen atmosphere for 18 hours
  2. customThe methanol is removed in vacuo
  3. customThe chloroform layer is separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-85b47922ec704bb6a4ee4cdd31031a60
Source dataset
uspto-grants-1980_10
Patent number
US04229456

Reaction notes

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