Ammonium Chloride → Methyl 2-methoxy-1,8-naphthyridine-3-carboxylate

HRID 1961445Notes

Reaction equation

HRID 1961445 reaction equation
Cl[C:2]1[C:11]([C:12]([O:14][CH2:15]C)=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:17][O-:18].[Na+].[NH4+].[Cl-]>CO>[CH3:17][O:18][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 15067503Ethyl 2-chloro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 66633977Methyl 2-methoxy-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethyl 2-chloro-1,8-naphthyridine-3-carboxylate (104.0 mg, 0.44 mmol) was dissolved in anhydrous MeOH under N2. NaOMe (33.2 mg, 0.62 mmol) was added as a solution in MeOH. The mixture was refluxed for 15 h, and then it was allowed to cool. NH4Cl (sat) was added and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated to yield 102.0 mg (quant) of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 15 h
  2. temperatureto cool
  3. extractionthe product extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-24bb70f2a26f45e8a37425930245cdb3
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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