N-bromobutanimide → HCID 86714158, compound

HRID 919957Notes

Reaction equation

HRID 919957 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:23])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH3:15])[C:10](=[O:16])[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:8]2)=[O:4].[Br:24]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:23])=[C:7]2[C:12](=[C:13]([Br:24])[N:14]=1)[N:11]([CH3:15])[C:10](=[O:16])[C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:8]2)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68297576HCID 68297576, compound

Product 1

HCID 86714158HCID 86714158, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-hydroxy-1-methyl-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (67 mg, 0.216 mmol) and N-bromosuccinimide (42 mg, 0.238 mmol) in CH2Cl2 (1 mL) was refluxed for 3 h. Solvent was evaporated in vacuo, and the residue was purified by silica gel chromatography (5-40% EtOAc/hexanes+1% AcOH) to give 69 mg of the title compound as a yellow solid. MS: (−) m/z 387.13, 389.15 (M-1, 79/81Br).

Workup

  1. temperaturewas refluxed for 3 h
  2. customSolvent was evaporated in vacuo
  3. customthe residue was purified by silica gel chromatography (5-40% EtOAc/hexanes+1% AcOH)

Sources & evidence

ORD record
ord-645f04edf0dc4ddfa5d2f0d443f42092
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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