Methyl 6-(methyloxy)-1,5-naphthyridine-3-carboxylate → Methyl 6-oxo-5,6-dihydro-1,5-naphthyridine-3-carboxylate

HRID 656920Notes

Reaction equation

HRID 656920 reaction equation
C[O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]([O:15][CH3:16])=[O:14])=[CH:6]2>Br.C(O)(=O)C>[O:2]=[C:3]1[CH:12]=[CH:11][C:10]2[N:9]=[CH:8][C:7]([C:13]([O:15][CH3:16])=[O:14])=[CH:6][C:5]=2[NH:4]1

Participants

4

Reactant 1

HCID 68817307Methyl 6-(methyloxy)-1,5-naphthyridine-3-carboxylate

Product 1

HCID 68818275Methyl 6-oxo-5,6-dihydro-1,5-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A mixture of methyl 6-(methyloxy)-1,5-naphthyridine-3-carboxylate (1.45 g, 6.65 mmol) in 30% HBr in acetic acid (40 ml) was stirred at rt for 18 h before evaporation and drying in vacuo. The solid was washed with Et2O and dried in vacuo to give the desired product as the dihydrobromide salt (2.425 g, 99%).

Workup

  1. customdrying in vacuo
  2. washThe solid was washed with Et2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-4f091e81713d4d5dbac42b43f9893fd8
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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