Benzyl Bromide → 5-Benzyloxy-8-nitro-quinoline

HRID 513798Notes

Reaction equation

HRID 513798 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[N+:15]([C:18]1[C:27]2[N:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]([OH:28])=[CH:20][CH:19]=1)([O-:17])=[O:16]>CN(C=O)C.O>[CH2:2]([O:28][C:21]1[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[C:27]2[C:22]=1[CH:23]=[CH:24][CH:25]=[N:26]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 52973548-Nitroquinolin-5-ol

Product 1

HCID 681832585-Benzyloxy-8-nitro-quinolineYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Bromomethyl-benzene (424 μl, 3.57 mmol) and K2CO3 (493 mg, 3.57 mmol) were added to a solution of 8-nitro-quinolin-5-ol 563 (566 mg, 2.98 mmol) in DMF (5 ml) and the mixture was heated at 90° C. for 6 h. After cooling, the mixture was diluted with water (25 ml) and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine (25 ml), dried (Na2SO4) and concentrated in vacuo to give the title compound (572 mg, 69%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe combined organic phases were washed with brine (25 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9066617c1b1418c863d1d45f1efddac
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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