Water → HCID 67009622, compound

HRID 2194514Notes

Reaction equation

HRID 2194514 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:3]1=[O:16].[Br:17]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:3]1=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimide2×HCID 67010726HCID 67010726, compound

Product 1

HCID 67009622HCID 67009622, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

10.71 g (49.0 mmol) of methyl 1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in carbon tetrachloride (200 mL), and 8.64 g (49.0 mmol) of N-bromosuccinimide and 0.1 g of 1,2-azobis(2-methylpropionitrile) were added thereto. While the mixture was irradiated with light, the mixture was stirred for 4 hours. 3.0 g (17.0 mmol) of N-bromosuccinimide was further added to the mixture, and the resulting mixture was stirred for 3 hours while the mixture was irradiated with light. The reaction mixture was poured into water, and the mixture was extracted with chloroform. The organic phase was washed with water, dried, and concentrated. The residue was purified by column chromatography (ethyl acetate:chloroform=1:19), and thus 10.56 g (yield: 73%) of the title compound was obtained as colorless crystals.

Workup

  1. customWhile the mixture was irradiated with light
  2. stirringthe resulting mixture was stirred for 3 hours while the mixture
  3. customwas irradiated with light
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic phase was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (ethyl acetate:chloroform=1:19)

Sources & evidence

ORD record
ord-cca504e660764df1ad893ea4f7e40375
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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