Methylamine → Ethyl 2-(methylamino)-1,8-naphthyridine-3-carboxylate

HRID 1961447Notes

Reaction equation

HRID 1961447 reaction equation
Cl[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:17][NH2:18]>CCO>[CH3:17][NH:18][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 15067503Ethyl 2-chloro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 66745462Ethyl 2-(methylamino)-1,8-naphthyridine-3-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-chloro-1,8-naphthyridine-3-carboxylate (100 mg, 0.42 eq.) was dissolved in EtOH. MeNH2 (71.8 μl, 11.84 M aqueous solution) was added to the solution. The mixture was stirred at r.t. for 18 h. The solvents were removed under reduced pressure. The residue was dissolved in EtOAc and washed with water (×2). The organic extract was dried (MgSO4), filtered and concentrated to yield 60.2 mg (62%) of the title compound.

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water (×2)
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29c80a4c0947467fb4c6046a30b662eb
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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