Water → 3-Bromo-8-nitro-4-quinolinol

HRID 613457Notes

Reaction equation

HRID 613457 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[CH:3]1.[Br:15]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:15][C:3]1[C:2](=[O:1])[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 2885428-Nitroquinolin-4-ol

Product 1

HCID 123768613-Bromo-8-nitro-4-quinolinolYield 85.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

To a stirred mixture of 1,4-dihydro-4-oxo-8-nitroquinoline (10 g) in dimethylformamide (100 ml) was dropwise added N-bromosuccinimide (9.83 g) over the period of 2 minutes under ice-cooling, and the mixture was stirred for 30 minutes at 4° C. Water was added thereto under ice-cooling, and the mixture was stirred for 1 hour. The resulting precipitate was collected by filtration, and the residue was washed with water and hot ethanol to give 3-bromo-1,4-dihydro-8-nitro-4-oxoquinoline (12.12 g).

Workup

  1. customover the period of 2 minutes
  2. temperaturecooling
  3. temperatureunder ice-cooling
  4. stirringthe mixture was stirred for 1 hour
  5. filtrationThe resulting precipitate was collected by filtration
  6. washthe residue was washed with water and hot ethanol

Sources & evidence

ORD record
ord-6905dba4cf1e40ad8139fdd59654d76e
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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