6-Aminoquinoline → 5-Bromoquinolin-6-amine

HRID 386653Notes

Reaction equation

HRID 386653 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br-:12].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.CO>[Br:12][C:6]1[C:7]([NH2:11])=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2

Participants

6

Reactant 3

HCID 113736-AminoquinolineHCID 24477Sodium ThiosulfateHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 127412325-Bromoquinolin-6-amineYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of quinolin-6-ylamine (503 mg, 3.49 mmol) in dichloromethane (17 mL) and methanol (8.6 mL) was added tetra-n-butylammonium tribromide (1.68 g, 3.49 mmol). The mixture was stirred at 25° C. for 90 minutes, and then 10 5 mL of aqueous sodium thiosulfate was added. The mixture was extracted with dichloromethane, and the combined extracts were washed with water, dried (Na2SO4), filtered and concentrated to dryness under reduced pressure. Purification by flash column (hexanes/ethylacetate gradient) gave 5-bromo-quinolin-6-ylamine (246 mg, 32%).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe combined extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by flash column (hexanes/ethylacetate gradient)

Sources & evidence

ORD record
ord-baedc0ae213d4078870c0f88eb117d14
Source dataset
uspto-grants-2013_02
Patent number
US08372865B2

Reaction notes

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