N-bromobutanimide → HCID 86714191, compound

HRID 1411094Notes

Reaction equation

HRID 1411094 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:28])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10](=[O:21])[C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:8]2)=[O:4].[Br:29]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:28])=[C:7]2[C:12](=[C:13]([Br:29])[N:14]=1)[N:11]([CH2:15][CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])[C:10](=[O:21])[C:9]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:8]2)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68297209HCID 68297209, compound

Product 1

HCID 86714191HCID 86714191, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-ethyl-butyl)-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (200 mg, 0.53 mmol) and N-bromosuccinimide (103 mg, 0.58 mmol) in CH2Cl2 (2 mL) was refluxed for 3 h. Solvent was evaporated in vacuo, and the residue was purified by silica gel chromatography (3-15% EtOAc/hexanes+1% AcOH) to give 156 mg of the title compound as a yellow solid. MS: (+) m/z 459.31, 461.13 (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 (3-15% EtOAc/hexanes+1% AcOH)

Sources & evidence

ORD record
ord-bb324a6448d145f79142de472cd9b894
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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