N-bromobutanimide → HCID 54679311, compound

HRID 522371Notes

Reaction equation

HRID 522371 reaction equation
[Br:1]N1C(=O)CCC1=O.[OH:9][C:10]1[CH:19]=[C:18]([OH:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1>C(Cl)Cl>[Br:1][C:19]1[C:10](=[O:9])[NH:11][C:12]2[C:17]([C:18]=1[OH:20])=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1785165532-hydroxy-1H-quinolin-4-one

Product 1

HCID 54679311HCID 54679311, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-bromosuccinimide (2.21 g) was added to the solution of 2,4-dihydroxyquinoline (2 g) in DCM (50 ml). The mixture was stirred at room temperature for 3 days. The mixture was filtrated and the solid was triturated with isopropanol. After filtration, toluene was added to the solid and the solvent was evaporated under reduced pressure to give the desired product (1.92 g) as a beige solid. LRMS (ES+) m/z 240.1 (M+H)+.

Workup

  1. filtrationThe mixture was filtrated
  2. customthe solid was triturated with isopropanol
  3. filtrationAfter filtration, toluene
  4. additionwas added to the solid
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-25160d1c85a8414aa1f6b2e53f60bb43
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

Loading…