Sodium Sulfite → HCID 178515288, compound

HRID 69044

Reaction equation

HRID 69044 reaction equation
[Br:1]N1C(=O)CCC1=O.[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Br:1][C:11]1[CH:12]=[N:13][C:14]2[C:19]([C:10]=1[OH:9])=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 178516385quinolin-4-ol

Product 1

HCID 178515288HCID 178515288, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Bromosuccinimide (1.3 g) was added to a DMF solution (15 ml) of 4-hydroxy quinoline (1.0 g) and the mixture was stirred at room temperature for 15 hours. A sodium hydrogencarbonate aqueous solution of 25% sodium sulfite was added to the mixture. The mixture was stirred and the precipitated insoluble matter was separated. The filtrate was dissolved in a mixture of ethyl acetate and methanol, and an insoluble matter was removed by filtration. The filtrate was condensed under reduced pressure, and the residue was washed with ethyl acetate and dried to give the title compound (1.1 g) as a white powder.

Workup

  1. stirringThe mixture was stirred
  2. customthe precipitated insoluble matter was separated
  3. dissolutionThe filtrate was dissolved in a mixture of ethyl acetate and methanol
  4. customan insoluble matter was removed by filtration
  5. customcondensed under reduced pressure
  6. washthe residue was washed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-216f17993b204565b8b69a733f2d9dec
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Linked notes

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