N-bromobutanimide → Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate

HRID 897289Notes

Reaction equation

HRID 897289 reaction equation
[OH:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Br:16]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:15][O:14][C:12]([C:3]1[C:2]([OH:1])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[C:5]([Br:16])[N:4]=1)=[O:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22346294Methyl 8-hydroxy-1,6-naphthyridine-7-carboxylate

Product 1

HCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 8-hydroxy-1,6-naphthyridine-7-carboxylate from Example 1 Step 2 (5.0 g, 24.49 mmol) in CH2Cl2 (100 ml) at room temperature was added N-bromo succinimide (4.36 g, 24.49 mmol). The reaction was stirred for 1 hr. The solids were collected by filtration and dried in vacuo to afford the title compound as an off white solid.

Workup

  1. filtrationThe solids were collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-50658384c79e4c8a8fe54e588451ee6b
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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