N-bromobutanimide → 6-Amino-7-bromo-quinoline-5-carboxylic acid methyl ester

HRID 245649Notes

Reaction equation

HRID 245649 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[CH:12]=[CH:13][C:14]=1[NH2:15])=[O:4].[Br:16]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:11]=2[CH:12]=[C:13]([Br:16])[C:14]=1[NH2:15])=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 45089602Methyl 6-aminoquinoline-5-carboxylate

Product 1

HCID 579900906-Amino-7-bromo-quinoline-5-carboxylic acid methyl esterYield 31.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6.6 g (32.6 mmol) of 6-amino-quinoline-5-carboxylic acid methyl ester, prepared as in step b in example 45, in 50 mL of N,N-dimethylformamide is added 5.80 g (17.78 mmol) of N-bromosuccinimide. The reaction is stirred at ambient temperature for 4 hours. The solvent is then evaporated and the residue is submitted to column chromatography purification on silica gel with ethyl acetate as eluent to afford 1.59 g (17%) of the product as a yellow solid; LC/MS:281/283 (M+H)+.

Workup

  1. customThe solvent is then evaporated
  2. customthe residue is submitted to column chromatography purification on silica gel with ethyl acetate as eluent

Sources & evidence

ORD record
ord-7990266fa2f24e21abe1c97af5799e2a
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

Loading…